NPASS Compound

Structure

CID275583 OpenBabel06191716082D 26 29 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2084 -1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4265 -1.2515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.5860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0376 -1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.5860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2557 -1.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 9 2 1 1 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 20 1 6 0 0 0 11 19 1 1 0 0 0 12 18 1 0 0 0 0 12 21 2 0 0 0 0 13 19 1 1 0 0 0 13 26 1 0 0 0 0 14 22 2 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 1 0 0 0 16 17 1 0 0 0 0 16 24 2 0 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 20 1 6 0 0 0 18 25 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	362.446
LogP:	1.335
LogD:	0.779
LogS:	-2.677
# Rotatable Bonds:	0
TPSA:	97.74
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	5.17
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056
MDCK Permeability:	7.296176045201719e-05
Pgp-inhibitor:	0.949
Pgp-substrate:	0.081
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	58.38432312011719%
Volume Distribution (VD):	0.404
Pgp-substrate:	49.176727294921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.4
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.652
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	15.537
Half-life (T1/2):	0.225

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.393
Drug-inuced Liver Injury (DILI):	0.796
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.241
Maximum Recommended Daily Dose:	0.283
Skin Sensitization:	0.188
Carcinogencity:	0.208
Eye Corrosion:	0.041
Eye Irritation:	0.023
Respiratory Toxicity:	0.936

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC275583

Natural Product ID:	NPC275583
*Common Name:**	JFBCRMVSRHYIIU-SONCKRQGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JFBCRMVSRHYIIU-SONCKRQGSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-8-5-12(21)18(25)20(4)10(8)6-13-19(3)11(7-14(22)26-13)9(2)15(23)16(24)17(19)20/h5,9-11,13,15,17-18,23,25H,6-7H2,1-4H3/t9-,10+,11+,13-,15-,17+,18-,19-,20+/m1/s1
SMILES:	O=C1O[C@@H]2C[C@H]3C(=CC(=O)[C@H]([C@@]3([C@@H]3[C@@]2([C@@H](C1)[C@@H](C)[C@H](C3=O)O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3120499
PubChem CID:	76332506
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19659728]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368118]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667820]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9375	Medium grandiflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3576	Bersama swinnyi	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1900.0	nM	PMID[571143]
NPT2	Others	Unspecified		Inhibition	>	50.0	%	PMID[571143]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC275583 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	1420
0.2-0.3	4489
0.3-0.4	8543
0.4-0.5	12621
0.5-0.6	7093
0.6-0.7	4905
0.7-0.8	3018
0.8-0.85	310
0.85-0.9	55
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9278	High Similarity	NPC472972
0.902	High Similarity	NPC293850
0.8942	High Similarity	NPC34315
0.8922	High Similarity	NPC144854
0.8922	High Similarity	NPC3316
0.8835	High Similarity	NPC192813
0.8835	High Similarity	NPC277017
0.8835	High Similarity	NPC154608
0.8824	High Similarity	NPC181357
0.8812	High Similarity	NPC95585
0.8812	High Similarity	NPC282233
0.8774	High Similarity	NPC49451
0.8762	High Similarity	NPC201992
0.8762	High Similarity	NPC146945
0.8762	High Similarity	NPC171888
0.8692	High Similarity	NPC473798
0.8679	High Similarity	NPC11252
0.8679	High Similarity	NPC289312
0.8641	High Similarity	NPC102352
0.8624	High Similarity	NPC17772
0.8611	High Similarity	NPC40632
0.8611	High Similarity	NPC328374
0.8611	High Similarity	NPC96312
0.8611	High Similarity	NPC251236
0.8598	High Similarity	NPC51978
0.8598	High Similarity	NPC208998
0.8598	High Similarity	NPC7921
0.8571	High Similarity	NPC27814
0.8559	High Similarity	NPC470921
0.8558	High Similarity	NPC202524
0.8532	High Similarity	NPC97908
0.8532	High Similarity	NPC122033
0.8532	High Similarity	NPC287343
0.8532	High Similarity	NPC470854
0.8532	High Similarity	NPC474654
0.8519	High Similarity	NPC18547
0.8519	High Similarity	NPC474906
0.8515	High Similarity	NPC104861
0.8491	Intermediate Similarity	NPC210005
0.8476	Intermediate Similarity	NPC189075
0.8476	Intermediate Similarity	NPC94529
0.8476	Intermediate Similarity	NPC275539
0.8455	Intermediate Similarity	NPC251310
0.8447	Intermediate Similarity	NPC179208
0.8447	Intermediate Similarity	NPC95899
0.8447	Intermediate Similarity	NPC478057
0.844	Intermediate Similarity	NPC235539
0.844	Intermediate Similarity	NPC134869
0.844	Intermediate Similarity	NPC152199
0.8426	Intermediate Similarity	NPC194100
0.8416	Intermediate Similarity	NPC260149
0.8416	Intermediate Similarity	NPC58942
0.8416	Intermediate Similarity	NPC114274
0.8416	Intermediate Similarity	NPC475876
0.8416	Intermediate Similarity	NPC478056
0.8396	Intermediate Similarity	NPC286174
0.8396	Intermediate Similarity	NPC77947
0.8396	Intermediate Similarity	NPC310546
0.8396	Intermediate Similarity	NPC250018
0.8396	Intermediate Similarity	NPC141350
0.8381	Intermediate Similarity	NPC110496
0.8378	Intermediate Similarity	NPC470777
0.8365	Intermediate Similarity	NPC474558
0.8364	Intermediate Similarity	NPC309433
0.8364	Intermediate Similarity	NPC472927
0.8333	Intermediate Similarity	NPC71348
0.8333	Intermediate Similarity	NPC88198
0.8333	Intermediate Similarity	NPC193948
0.8333	Intermediate Similarity	NPC474516
0.8318	Intermediate Similarity	NPC129689
0.8318	Intermediate Similarity	NPC197428
0.8317	Intermediate Similarity	NPC473456
0.8317	Intermediate Similarity	NPC170131
0.8317	Intermediate Similarity	NPC43747
0.8317	Intermediate Similarity	NPC226986
0.8302	Intermediate Similarity	NPC19412
0.8302	Intermediate Similarity	NPC476479
0.83	Intermediate Similarity	NPC473240
0.83	Intermediate Similarity	NPC139570
0.83	Intermediate Similarity	NPC474727
0.8288	Intermediate Similarity	NPC297179
0.8288	Intermediate Similarity	NPC188667
0.8288	Intermediate Similarity	NPC204552
0.8286	Intermediate Similarity	NPC231530
0.8286	Intermediate Similarity	NPC469607
0.8286	Intermediate Similarity	NPC278628
0.8283	Intermediate Similarity	NPC295643
0.8283	Intermediate Similarity	NPC477435
0.8283	Intermediate Similarity	NPC477436
0.8283	Intermediate Similarity	NPC272075
0.8283	Intermediate Similarity	NPC214756
0.8273	Intermediate Similarity	NPC207217
0.8273	Intermediate Similarity	NPC270958
0.8269	Intermediate Similarity	NPC159442
0.8269	Intermediate Similarity	NPC70967
0.8269	Intermediate Similarity	NPC251017
0.8269	Intermediate Similarity	NPC33973
0.8257	Intermediate Similarity	NPC474271
0.8257	Intermediate Similarity	NPC202889
0.8252	Intermediate Similarity	NPC81530
0.8252	Intermediate Similarity	NPC118964
0.8241	Intermediate Similarity	NPC115303
0.8241	Intermediate Similarity	NPC472928
0.8235	Intermediate Similarity	NPC471966
0.823	Intermediate Similarity	NPC102822
0.823	Intermediate Similarity	NPC477046
0.8224	Intermediate Similarity	NPC153239
0.8224	Intermediate Similarity	NPC470615
0.8218	Intermediate Similarity	NPC305483
0.8218	Intermediate Similarity	NPC96859
0.8218	Intermediate Similarity	NPC219353
0.8218	Intermediate Similarity	NPC157113
0.8218	Intermediate Similarity	NPC469545
0.8218	Intermediate Similarity	NPC62516
0.8218	Intermediate Similarity	NPC328162
0.8218	Intermediate Similarity	NPC476327
0.8218	Intermediate Similarity	NPC5532
0.8218	Intermediate Similarity	NPC476318
0.8218	Intermediate Similarity	NPC61369
0.8214	Intermediate Similarity	NPC475775
0.8214	Intermediate Similarity	NPC476529
0.8214	Intermediate Similarity	NPC472933
0.8208	Intermediate Similarity	NPC230541
0.82	Intermediate Similarity	NPC196485
0.82	Intermediate Similarity	NPC245972
0.82	Intermediate Similarity	NPC74751
0.819	Intermediate Similarity	NPC2436
0.819	Intermediate Similarity	NPC213366
0.819	Intermediate Similarity	NPC216245
0.819	Intermediate Similarity	NPC96268
0.819	Intermediate Similarity	NPC135854
0.819	Intermediate Similarity	NPC29705
0.819	Intermediate Similarity	NPC470251
0.8182	Intermediate Similarity	NPC145067
0.8182	Intermediate Similarity	NPC143268
0.8182	Intermediate Similarity	NPC4036
0.8182	Intermediate Similarity	NPC474525
0.8182	Intermediate Similarity	NPC45218
0.8182	Intermediate Similarity	NPC268238
0.8182	Intermediate Similarity	NPC233455
0.8182	Intermediate Similarity	NPC243354
0.8182	Intermediate Similarity	NPC158030
0.8182	Intermediate Similarity	NPC323821
0.8182	Intermediate Similarity	NPC198054
0.8182	Intermediate Similarity	NPC168027
0.8182	Intermediate Similarity	NPC65120
0.8182	Intermediate Similarity	NPC185936
0.8174	Intermediate Similarity	NPC24651
0.8173	Intermediate Similarity	NPC136289
0.8173	Intermediate Similarity	NPC163249
0.8165	Intermediate Similarity	NPC12046
0.8165	Intermediate Similarity	NPC205534
0.8165	Intermediate Similarity	NPC302146
0.8165	Intermediate Similarity	NPC280782
0.8165	Intermediate Similarity	NPC194951
0.8158	Intermediate Similarity	NPC312833
0.8155	Intermediate Similarity	NPC157787
0.8155	Intermediate Similarity	NPC46761
0.8155	Intermediate Similarity	NPC471727
0.8148	Intermediate Similarity	NPC473036
0.8148	Intermediate Similarity	NPC286880
0.8148	Intermediate Similarity	NPC272898
0.8142	Intermediate Similarity	NPC109973
0.8142	Intermediate Similarity	NPC107338
0.8142	Intermediate Similarity	NPC109607
0.8142	Intermediate Similarity	NPC112038
0.8137	Intermediate Similarity	NPC23680
0.8137	Intermediate Similarity	NPC476878
0.8137	Intermediate Similarity	NPC476879
0.8137	Intermediate Similarity	NPC108078
0.8137	Intermediate Similarity	NPC189880
0.8137	Intermediate Similarity	NPC89225
0.8131	Intermediate Similarity	NPC295244
0.8125	Intermediate Similarity	NPC118638
0.8125	Intermediate Similarity	NPC470776
0.8119	Intermediate Similarity	NPC470016
0.8119	Intermediate Similarity	NPC477438
0.8119	Intermediate Similarity	NPC317586
0.8119	Intermediate Similarity	NPC477437
0.8119	Intermediate Similarity	NPC274417
0.8113	Intermediate Similarity	NPC292588
0.8113	Intermediate Similarity	NPC51452
0.8113	Intermediate Similarity	NPC196528
0.8108	Intermediate Similarity	NPC173686
0.8108	Intermediate Similarity	NPC474734
0.8108	Intermediate Similarity	NPC16081
0.8095	Intermediate Similarity	NPC216114
0.8095	Intermediate Similarity	NPC254202
0.8095	Intermediate Similarity	NPC264048
0.8095	Intermediate Similarity	NPC140723
0.8091	Intermediate Similarity	NPC25909
0.8091	Intermediate Similarity	NPC472926
0.8091	Intermediate Similarity	NPC157441
0.8091	Intermediate Similarity	NPC194273
0.8087	Intermediate Similarity	NPC18945
0.8087	Intermediate Similarity	NPC265557
0.8087	Intermediate Similarity	NPC67251
0.8087	Intermediate Similarity	NPC105926
0.8087	Intermediate Similarity	NPC91693
0.8081	Intermediate Similarity	NPC46441

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC275583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1711
0.2-0.3	3685
0.3-0.4	2257
0.4-0.5	790
0.5-0.6	245
0.6-0.7	136
0.7-0.8	114
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.82	Intermediate Similarity	NPD7748	Approved
0.8182	Intermediate Similarity	NPD7515	Phase 2
0.8137	Intermediate Similarity	NPD7902	Approved
0.8113	Intermediate Similarity	NPD5739	Approved
0.8113	Intermediate Similarity	NPD6675	Approved
0.8113	Intermediate Similarity	NPD6402	Approved
0.8113	Intermediate Similarity	NPD7128	Approved
0.8056	Intermediate Similarity	NPD6372	Approved
0.8056	Intermediate Similarity	NPD6373	Approved
0.8039	Intermediate Similarity	NPD4697	Phase 3
0.8037	Intermediate Similarity	NPD5697	Approved
0.8037	Intermediate Similarity	NPD5701	Approved
0.7963	Intermediate Similarity	NPD7320	Approved
0.7963	Intermediate Similarity	NPD6011	Approved
0.7963	Intermediate Similarity	NPD6899	Approved
0.7963	Intermediate Similarity	NPD6881	Approved
0.7959	Intermediate Similarity	NPD3573	Approved
0.7944	Intermediate Similarity	NPD6008	Approved
0.7931	Intermediate Similarity	NPD8328	Phase 3
0.7928	Intermediate Similarity	NPD4632	Approved
0.7909	Intermediate Similarity	NPD6650	Approved
0.7909	Intermediate Similarity	NPD6649	Approved
0.789	Intermediate Similarity	NPD6013	Approved
0.789	Intermediate Similarity	NPD6012	Approved
0.789	Intermediate Similarity	NPD6014	Approved
0.7885	Intermediate Similarity	NPD5696	Approved
0.7864	Intermediate Similarity	NPD5221	Approved
0.7864	Intermediate Similarity	NPD5222	Approved
0.7864	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3618	Phase 1
0.7843	Intermediate Similarity	NPD7900	Approved
0.7843	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7102	Approved
0.7818	Intermediate Similarity	NPD6883	Approved
0.7818	Intermediate Similarity	NPD7290	Approved
0.78	Intermediate Similarity	NPD5328	Approved
0.7788	Intermediate Similarity	NPD4755	Approved
0.7788	Intermediate Similarity	NPD5173	Approved
0.7748	Intermediate Similarity	NPD6847	Approved
0.7748	Intermediate Similarity	NPD8130	Phase 1
0.7748	Intermediate Similarity	NPD6617	Approved
0.7748	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6869	Approved
0.7745	Intermediate Similarity	NPD6399	Phase 3
0.7719	Intermediate Similarity	NPD6009	Approved
0.7714	Intermediate Similarity	NPD7638	Approved
0.7679	Intermediate Similarity	NPD6882	Approved
0.7679	Intermediate Similarity	NPD8297	Approved
0.7672	Intermediate Similarity	NPD6319	Approved
0.7647	Intermediate Similarity	NPD6079	Approved
0.7642	Intermediate Similarity	NPD4700	Approved
0.7642	Intermediate Similarity	NPD5286	Approved
0.7642	Intermediate Similarity	NPD4696	Approved
0.7642	Intermediate Similarity	NPD5285	Approved
0.7642	Intermediate Similarity	NPD7640	Approved
0.7642	Intermediate Similarity	NPD7639	Approved
0.7619	Intermediate Similarity	NPD6083	Phase 2
0.7619	Intermediate Similarity	NPD6084	Phase 2
0.7607	Intermediate Similarity	NPD5983	Phase 2
0.757	Intermediate Similarity	NPD5223	Approved
0.7565	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD6672	Approved
0.7525	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.7479	Intermediate Similarity	NPD7604	Phase 2
0.7478	Intermediate Similarity	NPD6274	Approved
0.7478	Intermediate Similarity	NPD6868	Approved
0.7477	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6411	Approved
0.7451	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD3667	Approved
0.7431	Intermediate Similarity	NPD4754	Approved
0.7431	Intermediate Similarity	NPD5175	Approved
0.7431	Intermediate Similarity	NPD5174	Approved
0.7429	Intermediate Similarity	NPD4629	Approved
0.7429	Intermediate Similarity	NPD5210	Approved
0.7429	Intermediate Similarity	NPD5695	Phase 3
0.7423	Intermediate Similarity	NPD4695	Discontinued
0.7417	Intermediate Similarity	NPD7492	Approved
0.7414	Intermediate Similarity	NPD6317	Approved
0.7411	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6412	Phase 2
0.7377	Intermediate Similarity	NPD7736	Approved
0.7373	Intermediate Similarity	NPD6059	Approved
0.7373	Intermediate Similarity	NPD6054	Approved
0.7364	Intermediate Similarity	NPD5141	Approved
0.7355	Intermediate Similarity	NPD6616	Approved
0.7355	Intermediate Similarity	NPD6336	Discontinued
0.7353	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6314	Approved
0.735	Intermediate Similarity	NPD6335	Approved
0.735	Intermediate Similarity	NPD6313	Approved
0.7345	Intermediate Similarity	NPD4634	Approved
0.7327	Intermediate Similarity	NPD6409	Approved
0.7327	Intermediate Similarity	NPD6684	Approved
0.7327	Intermediate Similarity	NPD7146	Approved
0.7327	Intermediate Similarity	NPD7521	Approved
0.7327	Intermediate Similarity	NPD7334	Approved
0.7327	Intermediate Similarity	NPD5330	Approved
0.7311	Intermediate Similarity	NPD6016	Approved
0.7311	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6015	Approved
0.73	Intermediate Similarity	NPD3665	Phase 1
0.73	Intermediate Similarity	NPD3133	Approved
0.73	Intermediate Similarity	NPD3666	Approved
0.73	Intermediate Similarity	NPD4786	Approved
0.7297	Intermediate Similarity	NPD4768	Approved
0.7297	Intermediate Similarity	NPD4767	Approved
0.7295	Intermediate Similarity	NPD7078	Approved
0.7295	Intermediate Similarity	NPD8293	Discontinued
0.7288	Intermediate Similarity	NPD7101	Approved
0.7288	Intermediate Similarity	NPD7100	Approved
0.7282	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4753	Phase 2
0.7282	Intermediate Similarity	NPD6101	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.725	Intermediate Similarity	NPD6370	Approved
0.725	Intermediate Similarity	NPD5988	Approved
0.7238	Intermediate Similarity	NPD4202	Approved
0.7184	Intermediate Similarity	NPD6903	Approved
0.7168	Intermediate Similarity	NPD4729	Approved
0.7168	Intermediate Similarity	NPD5128	Approved
0.7168	Intermediate Similarity	NPD4730	Approved
0.7168	Intermediate Similarity	NPD5168	Approved
0.7167	Intermediate Similarity	NPD6908	Approved
0.7167	Intermediate Similarity	NPD6909	Approved
0.7157	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7115	Intermediate Similarity	NPD6673	Approved
0.7115	Intermediate Similarity	NPD6080	Approved
0.7115	Intermediate Similarity	NPD6904	Approved
0.7105	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5778	Approved
0.7075	Intermediate Similarity	NPD5779	Approved
0.7073	Intermediate Similarity	NPD7507	Approved
0.7064	Intermediate Similarity	NPD4225	Approved
0.7063	Intermediate Similarity	NPD7260	Phase 2
0.7059	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5251	Approved
0.7043	Intermediate Similarity	NPD5247	Approved
0.7043	Intermediate Similarity	NPD5248	Approved
0.7043	Intermediate Similarity	NPD5135	Approved
0.7043	Intermediate Similarity	NPD5169	Approved
0.7043	Intermediate Similarity	NPD5249	Phase 3
0.7043	Intermediate Similarity	NPD5250	Approved
0.7043	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7614	Phase 1
0.7027	Intermediate Similarity	NPD7632	Discontinued
0.7018	Intermediate Similarity	NPD6686	Approved
0.7009	Intermediate Similarity	NPD5282	Discontinued
0.699	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5217	Approved
0.6983	Remote Similarity	NPD5127	Approved
0.6983	Remote Similarity	NPD5216	Approved
0.6983	Remote Similarity	NPD5215	Approved
0.6981	Remote Similarity	NPD5693	Phase 1
0.6961	Remote Similarity	NPD3668	Phase 3
0.6961	Remote Similarity	NPD4197	Approved
0.696	Remote Similarity	NPD6033	Approved
0.6905	Remote Similarity	NPD7319	Approved
0.6893	Remote Similarity	NPD5329	Approved
0.6893	Remote Similarity	NPD1694	Approved
0.6887	Remote Similarity	NPD5692	Phase 3
0.6881	Remote Similarity	NPD7732	Phase 3
0.6869	Remote Similarity	NPD3617	Approved
0.6852	Remote Similarity	NPD6001	Approved
0.6827	Remote Similarity	NPD6098	Approved
0.6822	Remote Similarity	NPD6050	Approved
0.6822	Remote Similarity	NPD5281	Approved
0.6822	Remote Similarity	NPD5284	Approved
0.6822	Remote Similarity	NPD5694	Approved
0.6807	Remote Similarity	NPD5167	Approved
0.68	Remote Similarity	NPD7645	Phase 2
0.6783	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6053	Discontinued
0.6765	Remote Similarity	NPD4223	Phase 3
0.6765	Remote Similarity	NPD4221	Approved
0.6765	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6921	Approved
0.6744	Remote Similarity	NPD6845	Suspended
0.6742	Remote Similarity	NPD6333	Approved
0.6742	Remote Similarity	NPD6334	Approved
0.6733	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.664	Remote Similarity	NPD6067	Discontinued
0.6638	Remote Similarity	NPD6614	Approved
0.6636	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5091	Approved
0.6574	Remote Similarity	NPD46	Approved
0.6574	Remote Similarity	NPD5207	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data