NPASS Compound

Structure

CID154608 OpenBabel06191715522D 25 28 0 0 1 0 0 0 0 0999 V2000 4.8911 -0.4389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4868 -0.2352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9080 -1.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8985 1.2932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1501 -1.7334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3996 0.4332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1501 -0.8668 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0964 -0.0471 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3996 -0.4335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3996 -2.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6490 0.8665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2211 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2208 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3760 -0.7808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8985 -0.4335 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6490 -1.7334 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3761 0.7808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6490 -0.8668 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8985 0.4332 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3996 -3.0224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6490 1.7222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4121 -1.8122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9080 -2.1612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1601 1.4532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 7 1 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 1 1 6 0 0 0 7 9 1 0 0 0 0 8 2 1 1 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 20 2 0 0 0 0 11 19 1 0 0 0 0 11 21 2 0 0 0 0 12 17 1 0 0 0 0 12 19 1 6 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 1 0 0 0 14 25 1 6 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 18 1 1 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	345.15
LogP:	0.854
LogD:	0.957
LogS:	-3.984
# 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:	0.517
Synthetic Accessibility Score:	5.762
Fsp3:	0.789
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:	-4.935
MDCK Permeability:	6.19279671809636e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.335

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.962
Plasma Protein Binding (PPB):	58.816715240478516%
Volume Distribution (VD):	0.352
Pgp-substrate:	47.12828063964844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.749
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.221
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	10.688
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.729
Drug-inuced Liver Injury (DILI):	0.374
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.264
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.231
Carcinogencity:	0.077
Eye Corrosion:	0.018
Eye Irritation:	0.019
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC154608

Natural Product ID:	NPC154608
*Common Name:**	UHQUEEGNYNSHKI-QEIPJPASSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UHQUEEGNYNSHKI-QEIPJPASSA-N
Standard InCHI:	InChI=1S/C19H24O6/c1-7-5-10(20)16(23)18(3)9(7)6-11(21)19(4)12-8(2)14(25-17(12)24)13(22)15(18)19/h6-8,12-16,22-23H,5H2,1-4H3/t7-,8-,12-,13+,14-,15-,16-,18+,19+/m1/s1
SMILES:	O=C1C[C@@H](C)C2=CC(=O)[C@@]3([C@@H]([C@]2([C@@H]1O)C)[C@@H](O)[C@@H]1OC(=O)[C@H]3[C@H]1C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3120502
PubChem CID:	76314382
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
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[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	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]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	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]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	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]
NPO14280	Helichrysum angustifolium	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]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	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]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	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]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	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]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	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	=	18400.0	nM	PMID[558265]
NPT2	Others	Unspecified		Inhibition	>	50.0	%	PMID[558265]

☑ 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 NPC154608 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	214
0.1-0.2	1239
0.2-0.3	4116
0.3-0.4	7754
0.4-0.5	12567
0.5-0.6	6596
0.6-0.7	5826
0.7-0.8	3929
0.8-0.85	366
0.85-0.9	62
0.9-0.95	21
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC277017
1.0	High Similarity	NPC192813
0.9899	High Similarity	NPC3316
0.9899	High Similarity	NPC144854
0.9798	High Similarity	NPC102352
0.9608	High Similarity	NPC210005
0.951	High Similarity	NPC141350
0.9406	High Similarity	NPC181357
0.934	High Similarity	NPC207217
0.9333	High Similarity	NPC49451
0.9327	High Similarity	NPC201992
0.9314	High Similarity	NPC230541
0.9238	High Similarity	NPC289312
0.9238	High Similarity	NPC474516
0.9238	High Similarity	NPC11252
0.9223	High Similarity	NPC293850
0.9159	High Similarity	NPC40632
0.9159	High Similarity	NPC251236
0.9159	High Similarity	NPC96312
0.9159	High Similarity	NPC328374
0.9151	High Similarity	NPC51978
0.9143	High Similarity	NPC188738
0.9074	High Similarity	NPC97908
0.9074	High Similarity	NPC122033
0.9074	High Similarity	NPC470854
0.9074	High Similarity	NPC287343
0.9074	High Similarity	NPC474654
0.9065	High Similarity	NPC474906
0.9065	High Similarity	NPC473798
0.9065	High Similarity	NPC18547
0.9057	High Similarity	NPC472002
0.8991	High Similarity	NPC17772
0.8981	High Similarity	NPC152199
0.8981	High Similarity	NPC235539
0.8981	High Similarity	NPC134869
0.8857	High Similarity	NPC19412
0.8835	High Similarity	NPC275583
0.8818	High Similarity	NPC204552
0.8818	High Similarity	NPC297179
0.8818	High Similarity	NPC188667
0.8807	High Similarity	NPC478216
0.8807	High Similarity	NPC179626
0.88	High Similarity	NPC256227
0.8796	High Similarity	NPC7921
0.8796	High Similarity	NPC208998
0.8785	High Similarity	NPC146945
0.8785	High Similarity	NPC171888
0.8774	High Similarity	NPC27814
0.8774	High Similarity	NPC153239
0.875	High Similarity	NPC65523
0.875	High Similarity	NPC477046
0.875	High Similarity	NPC102822
0.8739	High Similarity	NPC476529
0.8739	High Similarity	NPC470777
0.8739	High Similarity	NPC475775
0.8725	High Similarity	NPC472972
0.8716	High Similarity	NPC117712
0.8704	High Similarity	NPC302146
0.8661	High Similarity	NPC109607
0.8661	High Similarity	NPC112038
0.8661	High Similarity	NPC107338
0.8654	High Similarity	NPC264048
0.8649	High Similarity	NPC251310
0.8636	High Similarity	NPC474734
0.8624	High Similarity	NPC194100
0.8598	High Similarity	NPC472534
0.8598	High Similarity	NPC310546
0.8598	High Similarity	NPC143706
0.8585	High Similarity	NPC202524
0.8571	High Similarity	NPC469488
0.8559	High Similarity	NPC176513
0.8559	High Similarity	NPC470775
0.8559	High Similarity	NPC473590
0.8559	High Similarity	NPC309433
0.8545	High Similarity	NPC243354
0.8545	High Similarity	NPC323821
0.8545	High Similarity	NPC143268
0.8545	High Similarity	NPC470919
0.8545	High Similarity	NPC469877
0.8545	High Similarity	NPC268238
0.8545	High Similarity	NPC45218
0.8532	High Similarity	NPC280782
0.8522	High Similarity	NPC24651
0.8519	High Similarity	NPC286880
0.8519	High Similarity	NPC5103
0.8509	High Similarity	NPC222688
0.8509	High Similarity	NPC312833
0.8505	High Similarity	NPC275539
0.8505	High Similarity	NPC189075
0.8496	Intermediate Similarity	NPC109973
0.8491	Intermediate Similarity	NPC469607
0.8491	Intermediate Similarity	NPC96377
0.8482	Intermediate Similarity	NPC470776
0.8476	Intermediate Similarity	NPC282233
0.8476	Intermediate Similarity	NPC95585
0.8468	Intermediate Similarity	NPC474046
0.8468	Intermediate Similarity	NPC16081
0.8468	Intermediate Similarity	NPC470628
0.8468	Intermediate Similarity	NPC173686
0.8468	Intermediate Similarity	NPC259306
0.8468	Intermediate Similarity	NPC266728
0.8468	Intermediate Similarity	NPC49492
0.8455	Intermediate Similarity	NPC962
0.8455	Intermediate Similarity	NPC250109
0.8455	Intermediate Similarity	NPC194273
0.844	Intermediate Similarity	NPC132790
0.844	Intermediate Similarity	NPC469655
0.844	Intermediate Similarity	NPC469656
0.844	Intermediate Similarity	NPC474846
0.844	Intermediate Similarity	NPC471243
0.844	Intermediate Similarity	NPC97939
0.844	Intermediate Similarity	NPC100329
0.844	Intermediate Similarity	NPC247031
0.8435	Intermediate Similarity	NPC105926
0.8435	Intermediate Similarity	NPC67251
0.8435	Intermediate Similarity	NPC18945
0.8435	Intermediate Similarity	NPC265557
0.8435	Intermediate Similarity	NPC91693
0.8426	Intermediate Similarity	NPC478210
0.8411	Intermediate Similarity	NPC59530
0.8411	Intermediate Similarity	NPC110496
0.8407	Intermediate Similarity	NPC475041
0.8396	Intermediate Similarity	NPC258532
0.8396	Intermediate Similarity	NPC471293
0.8396	Intermediate Similarity	NPC255309
0.8393	Intermediate Similarity	NPC284068
0.8393	Intermediate Similarity	NPC473968
0.8393	Intermediate Similarity	NPC53396
0.8393	Intermediate Similarity	NPC98249
0.8378	Intermediate Similarity	NPC247069
0.8364	Intermediate Similarity	NPC234042
0.8364	Intermediate Similarity	NPC152117
0.8364	Intermediate Similarity	NPC90769
0.8364	Intermediate Similarity	NPC269530
0.8364	Intermediate Similarity	NPC71348
0.8362	Intermediate Similarity	NPC470922
0.8362	Intermediate Similarity	NPC476729
0.8349	Intermediate Similarity	NPC478211
0.8349	Intermediate Similarity	NPC474567
0.8349	Intermediate Similarity	NPC239097
0.8349	Intermediate Similarity	NPC5284
0.8349	Intermediate Similarity	NPC253906
0.8333	Intermediate Similarity	NPC94942
0.8333	Intermediate Similarity	NPC94529
0.8319	Intermediate Similarity	NPC284707
0.8319	Intermediate Similarity	NPC106644
0.8318	Intermediate Similarity	NPC222833
0.8304	Intermediate Similarity	NPC270958
0.8302	Intermediate Similarity	NPC277074
0.8302	Intermediate Similarity	NPC140723
0.8302	Intermediate Similarity	NPC209298
0.8302	Intermediate Similarity	NPC159442
0.8288	Intermediate Similarity	NPC198539
0.8288	Intermediate Similarity	NPC471204
0.8288	Intermediate Similarity	NPC52634
0.8288	Intermediate Similarity	NPC475966
0.8288	Intermediate Similarity	NPC469463
0.8288	Intermediate Similarity	NPC202889
0.8288	Intermediate Similarity	NPC469454
0.8288	Intermediate Similarity	NPC469496
0.8286	Intermediate Similarity	NPC97435
0.8286	Intermediate Similarity	NPC252614
0.8286	Intermediate Similarity	NPC81530
0.8273	Intermediate Similarity	NPC304180
0.8273	Intermediate Similarity	NPC179798
0.8269	Intermediate Similarity	NPC114274
0.8261	Intermediate Similarity	NPC470921
0.8261	Intermediate Similarity	NPC470779
0.8252	Intermediate Similarity	NPC104568
0.8246	Intermediate Similarity	NPC268958
0.8241	Intermediate Similarity	NPC293512
0.823	Intermediate Similarity	NPC13713
0.823	Intermediate Similarity	NPC477116
0.823	Intermediate Similarity	NPC27999
0.823	Intermediate Similarity	NPC469684
0.823	Intermediate Similarity	NPC58662
0.8224	Intermediate Similarity	NPC475036
0.8224	Intermediate Similarity	NPC96268
0.8224	Intermediate Similarity	NPC29705
0.8224	Intermediate Similarity	NPC284865
0.8224	Intermediate Similarity	NPC301787
0.8214	Intermediate Similarity	NPC326542
0.8208	Intermediate Similarity	NPC136289
0.8208	Intermediate Similarity	NPC469606
0.8208	Intermediate Similarity	NPC273005
0.8208	Intermediate Similarity	NPC31058
0.8208	Intermediate Similarity	NPC295791
0.8205	Intermediate Similarity	NPC473255
0.8198	Intermediate Similarity	NPC205534
0.8198	Intermediate Similarity	NPC194951
0.8198	Intermediate Similarity	NPC476801
0.8198	Intermediate Similarity	NPC12046
0.8198	Intermediate Similarity	NPC207251
0.819	Intermediate Similarity	NPC470388
0.819	Intermediate Similarity	NPC316964
0.819	Intermediate Similarity	NPC269642
0.8182	Intermediate Similarity	NPC197428
0.8174	Intermediate Similarity	NPC478051
0.8173	Intermediate Similarity	NPC43686
0.8173	Intermediate Similarity	NPC226986

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 NPC154608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1523
0.2-0.3	3754
0.3-0.4	2340
0.4-0.5	808
0.5-0.6	243
0.6-0.7	135
0.7-0.8	128
0.8-0.85	33
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8455	Intermediate Similarity	NPD4632	Approved
0.8257	Intermediate Similarity	NPD6372	Approved
0.8257	Intermediate Similarity	NPD6373	Approved
0.8174	Intermediate Similarity	NPD6319	Approved
0.8148	Intermediate Similarity	NPD6675	Approved
0.8148	Intermediate Similarity	NPD7128	Approved
0.8148	Intermediate Similarity	NPD6008	Approved
0.8148	Intermediate Similarity	NPD6402	Approved
0.8148	Intermediate Similarity	NPD5739	Approved
0.8108	Intermediate Similarity	NPD6649	Approved
0.8108	Intermediate Similarity	NPD6650	Approved
0.8077	Intermediate Similarity	NPD4697	Phase 3
0.8073	Intermediate Similarity	NPD5701	Approved
0.8073	Intermediate Similarity	NPD5697	Approved
0.807	Intermediate Similarity	NPD6009	Approved
0.8036	Intermediate Similarity	NPD8297	Approved
0.8	Intermediate Similarity	NPD6899	Approved
0.8	Intermediate Similarity	NPD7902	Approved
0.8	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD6881	Approved
0.8	Intermediate Similarity	NPD7320	Approved
0.7966	Intermediate Similarity	NPD8328	Phase 3
0.7961	Intermediate Similarity	NPD6399	Phase 3
0.7949	Intermediate Similarity	NPD5983	Phase 2
0.7928	Intermediate Similarity	NPD6013	Approved
0.7928	Intermediate Similarity	NPD6014	Approved
0.7928	Intermediate Similarity	NPD6012	Approved
0.7899	Intermediate Similarity	NPD7492	Approved
0.7863	Intermediate Similarity	NPD6054	Approved
0.7863	Intermediate Similarity	NPD6059	Approved
0.7857	Intermediate Similarity	NPD6883	Approved
0.7857	Intermediate Similarity	NPD7290	Approved
0.7857	Intermediate Similarity	NPD7102	Approved
0.7838	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD6616	Approved
0.783	Intermediate Similarity	NPD4755	Approved
0.7815	Intermediate Similarity	NPD7604	Phase 2
0.7797	Intermediate Similarity	NPD6016	Approved
0.7797	Intermediate Similarity	NPD6015	Approved
0.7788	Intermediate Similarity	NPD6617	Approved
0.7788	Intermediate Similarity	NPD8130	Phase 1
0.7788	Intermediate Similarity	NPD6847	Approved
0.7788	Intermediate Similarity	NPD6869	Approved
0.7788	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD8293	Discontinued
0.7769	Intermediate Similarity	NPD7078	Approved
0.7768	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5221	Approved
0.7736	Intermediate Similarity	NPD5222	Approved
0.7731	Intermediate Similarity	NPD6370	Approved
0.7731	Intermediate Similarity	NPD5988	Approved
0.7723	Intermediate Similarity	NPD3618	Phase 1
0.7719	Intermediate Similarity	NPD6882	Approved
0.7714	Intermediate Similarity	NPD7900	Approved
0.7714	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7748	Approved
0.7705	Intermediate Similarity	NPD7736	Approved
0.7699	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD4634	Approved
0.7692	Intermediate Similarity	NPD7515	Phase 2
0.7686	Intermediate Similarity	NPD6336	Discontinued
0.7685	Intermediate Similarity	NPD4700	Approved
0.7685	Intermediate Similarity	NPD4696	Approved
0.7685	Intermediate Similarity	NPD5286	Approved
0.7685	Intermediate Similarity	NPD5285	Approved
0.767	Intermediate Similarity	NPD5328	Approved
0.7664	Intermediate Similarity	NPD5173	Approved
0.7615	Intermediate Similarity	NPD5223	Approved
0.7607	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7638	Approved
0.7593	Intermediate Similarity	NPD4225	Approved
0.7589	Intermediate Similarity	NPD6412	Phase 2
0.7545	Intermediate Similarity	NPD4633	Approved
0.7545	Intermediate Similarity	NPD5226	Approved
0.7545	Intermediate Similarity	NPD5224	Approved
0.7545	Intermediate Similarity	NPD5211	Phase 2
0.7545	Intermediate Similarity	NPD5225	Approved
0.7524	Intermediate Similarity	NPD6079	Approved
0.7523	Intermediate Similarity	NPD7640	Approved
0.7523	Intermediate Similarity	NPD7639	Approved
0.7521	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6084	Phase 2
0.7477	Intermediate Similarity	NPD5174	Approved
0.7477	Intermediate Similarity	NPD4754	Approved
0.7477	Intermediate Similarity	NPD5175	Approved
0.7458	Intermediate Similarity	NPD7115	Discovery
0.7458	Intermediate Similarity	NPD6317	Approved
0.7434	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5696	Approved
0.7419	Intermediate Similarity	NPD6033	Approved
0.7411	Intermediate Similarity	NPD5141	Approved
0.7404	Intermediate Similarity	NPD5737	Approved
0.7404	Intermediate Similarity	NPD6672	Approved
0.7395	Intermediate Similarity	NPD6313	Approved
0.7395	Intermediate Similarity	NPD6314	Approved
0.7395	Intermediate Similarity	NPD6335	Approved
0.7373	Intermediate Similarity	NPD6868	Approved
0.7368	Intermediate Similarity	NPD6686	Approved
0.7345	Intermediate Similarity	NPD4768	Approved
0.7345	Intermediate Similarity	NPD4767	Approved
0.7333	Intermediate Similarity	NPD7100	Approved
0.7333	Intermediate Similarity	NPD7101	Approved
0.7327	Intermediate Similarity	NPD3667	Approved
0.7315	Intermediate Similarity	NPD5695	Phase 3
0.7308	Intermediate Similarity	NPD3573	Approved
0.729	Intermediate Similarity	NPD4202	Approved
0.7258	Intermediate Similarity	NPD7507	Approved
0.7217	Intermediate Similarity	NPD5128	Approved
0.7217	Intermediate Similarity	NPD4730	Approved
0.7217	Intermediate Similarity	NPD4729	Approved
0.7213	Intermediate Similarity	NPD6908	Approved
0.7213	Intermediate Similarity	NPD6909	Approved
0.7212	Intermediate Similarity	NPD7146	Approved
0.7212	Intermediate Similarity	NPD6684	Approved
0.7212	Intermediate Similarity	NPD6409	Approved
0.7212	Intermediate Similarity	NPD7334	Approved
0.7212	Intermediate Similarity	NPD5330	Approved
0.7212	Intermediate Similarity	NPD7521	Approved
0.7196	Intermediate Similarity	NPD8034	Phase 2
0.7196	Intermediate Similarity	NPD8035	Phase 2
0.7184	Intermediate Similarity	NPD3133	Approved
0.7184	Intermediate Similarity	NPD4786	Approved
0.7184	Intermediate Similarity	NPD3666	Approved
0.7184	Intermediate Similarity	NPD3665	Phase 1
0.717	Intermediate Similarity	NPD4753	Phase 2
0.7156	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4695	Discontinued
0.7097	Intermediate Similarity	NPD6067	Discontinued
0.7094	Intermediate Similarity	NPD5169	Approved
0.7094	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5247	Approved
0.7094	Intermediate Similarity	NPD5250	Approved
0.7094	Intermediate Similarity	NPD5135	Approved
0.7094	Intermediate Similarity	NPD5248	Approved
0.7094	Intermediate Similarity	NPD5251	Approved
0.7094	Intermediate Similarity	NPD5249	Phase 3
0.7087	Intermediate Similarity	NPD7319	Approved
0.7075	Intermediate Similarity	NPD6903	Approved
0.7075	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6921	Approved
0.7069	Intermediate Similarity	NPD5168	Approved
0.7064	Intermediate Similarity	NPD5282	Discontinued
0.7048	Intermediate Similarity	NPD5279	Phase 3
0.7037	Intermediate Similarity	NPD6411	Approved
0.7034	Intermediate Similarity	NPD5215	Approved
0.7034	Intermediate Similarity	NPD5127	Approved
0.7034	Intermediate Similarity	NPD5217	Approved
0.7034	Intermediate Similarity	NPD5216	Approved
0.7009	Intermediate Similarity	NPD6080	Approved
0.7009	Intermediate Similarity	NPD6904	Approved
0.7009	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD5210	Approved
0.6977	Remote Similarity	NPD7260	Phase 2
0.6952	Remote Similarity	NPD1694	Approved
0.693	Remote Similarity	NPD7632	Discontinued
0.6909	Remote Similarity	NPD6001	Approved
0.6887	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5281	Approved
0.6881	Remote Similarity	NPD5284	Approved
0.6881	Remote Similarity	NPD5693	Phase 1
0.686	Remote Similarity	NPD5167	Approved
0.6857	Remote Similarity	NPD4197	Approved
0.6857	Remote Similarity	NPD3668	Phase 3
0.6852	Remote Similarity	NPD6101	Approved
0.6852	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6053	Discontinued
0.6818	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5779	Approved
0.68	Remote Similarity	NPD8513	Phase 3
0.68	Remote Similarity	NPD8515	Approved
0.68	Remote Similarity	NPD8517	Approved
0.68	Remote Similarity	NPD8516	Approved
0.6794	Remote Similarity	NPD6845	Suspended
0.6792	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5329	Approved
0.6791	Remote Similarity	NPD6333	Approved
0.6791	Remote Similarity	NPD6334	Approved
0.6789	Remote Similarity	NPD46	Approved
0.6789	Remote Similarity	NPD5692	Phase 3
0.6789	Remote Similarity	NPD6698	Approved
0.6774	Remote Similarity	NPD7516	Approved
0.6765	Remote Similarity	NPD3617	Approved
0.6729	Remote Similarity	NPD6098	Approved
0.6727	Remote Similarity	NPD6050	Approved
0.6727	Remote Similarity	NPD5694	Approved
0.6696	Remote Similarity	NPD5344	Discontinued
0.6695	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7327	Approved
0.6694	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	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