NPASS Compound

Structure

CID181357 OpenBabel06191715552D 26 29 0 0 1 0 0 0 0 0999 V2000 4.9195 -0.4415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4955 -0.2365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9191 -1.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9095 1.3006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1742 -1.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1742 -0.8718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1028 -0.0474 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4193 -2.1793 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4193 -0.4360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2282 0.9794 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4193 0.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2279 -0.9793 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3782 -0.7853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9095 -0.4360 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6644 -1.7435 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6644 0.8715 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3783 0.7854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6644 -0.8718 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9095 0.4357 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4193 -3.0399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1646 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4203 -1.8226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9191 -2.1738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6644 1.7322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1609 1.4616 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 1 6 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 7 2 1 1 0 0 0 7 10 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 8 20 1 6 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 10 19 1 6 0 0 0 11 16 1 0 0 0 0 11 21 2 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 1 0 0 0 13 26 1 6 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 18 1 1 0 0 0 15 23 1 0 0 0 0 16 19 1 1 0 0 0 16 24 1 0 0 0 0 17 25 2 0 0 0 0 17 26 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:	366.17
Volume:	356.577
LogP:	0.484
LogD:	0.573
LogS:	-3.043
# Rotatable Bonds:	0
TPSA:	121.13
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.954
Fsp3:	0.842
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:	-5.148
MDCK Permeability:	0.00010028609540313482
Pgp-inhibitor:	0.319
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	48.991817474365234%
Volume Distribution (VD):	0.437
Pgp-substrate:	32.76223373413086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.623
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	5.233
Half-life (T1/2):	0.507

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.775
Drug-inuced Liver Injury (DILI):	0.268
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.077
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC181357

Natural Product ID:	NPC181357
*Common Name:**	FOZORDLHHZVDRJ-HFZVJSDDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FOZORDLHHZVDRJ-HFZVJSDDSA-N
Standard InCHI:	InChI=1S/C19H26O7/c1-6-5-8(20)15(23)18(3)9(6)11(21)16(24)19(4)10-7(2)13(26-17(10)25)12(22)14(18)19/h7-8,10,12-16,20,22-24H,5H2,1-4H3/t7-,8+,10-,12+,13-,14-,15-,16+,18+,19+/m1/s1
SMILES:	O[C@H]1CC(=C2[C@@]([C@@H]1O)(C)[C@H]1[C@@H](O)[C@@H]3OC(=O)[C@H]([C@@]1([C@H](C2=O)O)C)[C@H]3C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081234
PubChem CID:	44612898
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	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	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]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
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]
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]
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]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	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]
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]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	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]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[486684]

☑ 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 NPC181357 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	241
0.1-0.2	1511
0.2-0.3	4892
0.3-0.4	8673
0.4-0.5	11914
0.5-0.6	6649
0.6-0.7	5829
0.7-0.8	2747
0.8-0.85	188
0.85-0.9	46
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC144854
0.95	High Similarity	NPC3316
0.9406	High Similarity	NPC154608
0.9406	High Similarity	NPC192813
0.9406	High Similarity	NPC277017
0.9208	High Similarity	NPC102352
0.9038	High Similarity	NPC210005
0.8962	High Similarity	NPC49451
0.8952	High Similarity	NPC201992
0.8942	High Similarity	NPC141350
0.8879	High Similarity	NPC323821
0.8879	High Similarity	NPC268238
0.8879	High Similarity	NPC45218
0.8879	High Similarity	NPC143268
0.8868	High Similarity	NPC474516
0.8868	High Similarity	NPC289312
0.8868	High Similarity	NPC11252
0.8846	High Similarity	NPC293850
0.8824	High Similarity	NPC275583
0.8807	High Similarity	NPC17772
0.8796	High Similarity	NPC96312
0.8796	High Similarity	NPC251236
0.8796	High Similarity	NPC40632
0.8796	High Similarity	NPC16081
0.8796	High Similarity	NPC328374
0.8796	High Similarity	NPC173686
0.8796	High Similarity	NPC207217
0.8785	High Similarity	NPC51978
0.875	High Similarity	NPC230541
0.8738	High Similarity	NPC65523
0.8727	High Similarity	NPC470777
0.8716	High Similarity	NPC474654
0.8716	High Similarity	NPC287343
0.8716	High Similarity	NPC97908
0.8716	High Similarity	NPC470854
0.8716	High Similarity	NPC122033
0.8704	High Similarity	NPC18547
0.8704	High Similarity	NPC474906
0.8704	High Similarity	NPC473798
0.8692	High Similarity	NPC472002
0.8667	High Similarity	NPC19412
0.8624	High Similarity	NPC152199
0.8624	High Similarity	NPC235539
0.8624	High Similarity	NPC134869
0.86	High Similarity	NPC256227
0.8598	High Similarity	NPC188738
0.8585	High Similarity	NPC27814
0.8585	High Similarity	NPC153239
0.8571	High Similarity	NPC202524
0.8505	High Similarity	NPC272898
0.8505	High Similarity	NPC473036
0.8491	Intermediate Similarity	NPC94942
0.8482	Intermediate Similarity	NPC109973
0.8468	Intermediate Similarity	NPC204552
0.8468	Intermediate Similarity	NPC297179
0.8468	Intermediate Similarity	NPC188667
0.8462	Intermediate Similarity	NPC264048
0.8455	Intermediate Similarity	NPC179626
0.8455	Intermediate Similarity	NPC478216
0.844	Intermediate Similarity	NPC7921
0.844	Intermediate Similarity	NPC208998
0.8426	Intermediate Similarity	NPC171888
0.8426	Intermediate Similarity	NPC146945
0.8411	Intermediate Similarity	NPC286174
0.8411	Intermediate Similarity	NPC77947
0.8407	Intermediate Similarity	NPC477046
0.8407	Intermediate Similarity	NPC102822
0.8393	Intermediate Similarity	NPC475775
0.8393	Intermediate Similarity	NPC268958
0.8393	Intermediate Similarity	NPC476529
0.8365	Intermediate Similarity	NPC295791
0.835	Intermediate Similarity	NPC472972
0.835	Intermediate Similarity	NPC88198
0.8349	Intermediate Similarity	NPC302146
0.8348	Intermediate Similarity	NPC24651
0.8333	Intermediate Similarity	NPC129689
0.8333	Intermediate Similarity	NPC312833
0.8333	Intermediate Similarity	NPC286880
0.8319	Intermediate Similarity	NPC109607
0.8319	Intermediate Similarity	NPC107338
0.8319	Intermediate Similarity	NPC112038
0.8304	Intermediate Similarity	NPC251310
0.8304	Intermediate Similarity	NPC470776
0.83	Intermediate Similarity	NPC477435
0.83	Intermediate Similarity	NPC477436
0.8288	Intermediate Similarity	NPC474734
0.8286	Intermediate Similarity	NPC251017
0.8286	Intermediate Similarity	NPC70967
0.8286	Intermediate Similarity	NPC33973
0.8273	Intermediate Similarity	NPC194100
0.8261	Intermediate Similarity	NPC67251
0.8261	Intermediate Similarity	NPC105926
0.8261	Intermediate Similarity	NPC265557
0.8261	Intermediate Similarity	NPC91693
0.8261	Intermediate Similarity	NPC18945
0.8257	Intermediate Similarity	NPC469656
0.8257	Intermediate Similarity	NPC132790
0.8257	Intermediate Similarity	NPC469655
0.8257	Intermediate Similarity	NPC474846
0.8257	Intermediate Similarity	NPC115303
0.8257	Intermediate Similarity	NPC100329
0.8257	Intermediate Similarity	NPC97939
0.8257	Intermediate Similarity	NPC247031
0.8241	Intermediate Similarity	NPC310546
0.8241	Intermediate Similarity	NPC478210
0.8241	Intermediate Similarity	NPC143706
0.8241	Intermediate Similarity	NPC472534
0.8235	Intermediate Similarity	NPC91439
0.823	Intermediate Similarity	NPC469488
0.8214	Intermediate Similarity	NPC470775
0.8214	Intermediate Similarity	NPC473590
0.8214	Intermediate Similarity	NPC309433
0.8214	Intermediate Similarity	NPC176513
0.8208	Intermediate Similarity	NPC2436
0.8208	Intermediate Similarity	NPC216245
0.8208	Intermediate Similarity	NPC135854
0.8208	Intermediate Similarity	NPC470251
0.8198	Intermediate Similarity	NPC243354
0.8198	Intermediate Similarity	NPC469877
0.8198	Intermediate Similarity	NPC117712
0.8198	Intermediate Similarity	NPC470919
0.819	Intermediate Similarity	NPC476729
0.8182	Intermediate Similarity	NPC269530
0.8182	Intermediate Similarity	NPC152117
0.8182	Intermediate Similarity	NPC234042
0.8182	Intermediate Similarity	NPC90769
0.8182	Intermediate Similarity	NPC280782
0.8182	Intermediate Similarity	NPC205534
0.8174	Intermediate Similarity	NPC222688
0.8173	Intermediate Similarity	NPC157787
0.8165	Intermediate Similarity	NPC478211
0.8165	Intermediate Similarity	NPC5284
0.8165	Intermediate Similarity	NPC5103
0.8148	Intermediate Similarity	NPC275539
0.8148	Intermediate Similarity	NPC189075
0.8142	Intermediate Similarity	NPC106644
0.8137	Intermediate Similarity	NPC477438
0.8137	Intermediate Similarity	NPC477437
0.8131	Intermediate Similarity	NPC469607
0.8131	Intermediate Similarity	NPC470587
0.8131	Intermediate Similarity	NPC96377
0.8131	Intermediate Similarity	NPC51452
0.8125	Intermediate Similarity	NPC259306
0.8125	Intermediate Similarity	NPC470628
0.8125	Intermediate Similarity	NPC474046
0.8125	Intermediate Similarity	NPC266728
0.8125	Intermediate Similarity	NPC49492
0.812	Intermediate Similarity	NPC87662
0.8113	Intermediate Similarity	NPC277074
0.8113	Intermediate Similarity	NPC159533
0.8113	Intermediate Similarity	NPC209298
0.8113	Intermediate Similarity	NPC159442
0.8108	Intermediate Similarity	NPC475966
0.8108	Intermediate Similarity	NPC250109
0.8108	Intermediate Similarity	NPC962
0.8108	Intermediate Similarity	NPC194273
0.8108	Intermediate Similarity	NPC474271
0.8108	Intermediate Similarity	NPC198539
0.8095	Intermediate Similarity	NPC124211
0.8095	Intermediate Similarity	NPC97435
0.8095	Intermediate Similarity	NPC252614
0.8091	Intermediate Similarity	NPC471243
0.8091	Intermediate Similarity	NPC34315
0.8087	Intermediate Similarity	NPC470921
0.8087	Intermediate Similarity	NPC470779
0.8077	Intermediate Similarity	NPC474724
0.807	Intermediate Similarity	NPC475041
0.8056	Intermediate Similarity	NPC473037
0.8056	Intermediate Similarity	NPC110496
0.8056	Intermediate Similarity	NPC59530
0.8053	Intermediate Similarity	NPC284068
0.8053	Intermediate Similarity	NPC27999
0.8053	Intermediate Similarity	NPC473968
0.8053	Intermediate Similarity	NPC477116
0.8053	Intermediate Similarity	NPC477252
0.8053	Intermediate Similarity	NPC58662
0.8053	Intermediate Similarity	NPC53396
0.8053	Intermediate Similarity	NPC98249
0.8053	Intermediate Similarity	NPC13713
0.8039	Intermediate Similarity	NPC477439
0.8037	Intermediate Similarity	NPC96268
0.8037	Intermediate Similarity	NPC258532
0.8037	Intermediate Similarity	NPC301787
0.8037	Intermediate Similarity	NPC471293
0.8037	Intermediate Similarity	NPC255309
0.8036	Intermediate Similarity	NPC299849
0.8036	Intermediate Similarity	NPC247069
0.8034	Intermediate Similarity	NPC470922
0.8019	Intermediate Similarity	NPC165250
0.8019	Intermediate Similarity	NPC53222
0.8019	Intermediate Similarity	NPC80781
0.8018	Intermediate Similarity	NPC473352
0.8018	Intermediate Similarity	NPC71348
0.8018	Intermediate Similarity	NPC193948
0.8	Intermediate Similarity	NPC474567
0.8	Intermediate Similarity	NPC239097
0.8	Intermediate Similarity	NPC470388
0.8	Intermediate Similarity	NPC307954
0.8	Intermediate Similarity	NPC253906
0.8	Intermediate Similarity	NPC316964

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 NPC181357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1895
0.2-0.3	3892
0.3-0.4	1991
0.4-0.5	668
0.5-0.6	226
0.6-0.7	136
0.7-0.8	125
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8108	Intermediate Similarity	NPD4632	Approved
0.7909	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6319	Approved
0.7798	Intermediate Similarity	NPD7128	Approved
0.7798	Intermediate Similarity	NPD5739	Approved
0.7798	Intermediate Similarity	NPD6675	Approved
0.7798	Intermediate Similarity	NPD6008	Approved
0.7798	Intermediate Similarity	NPD6402	Approved
0.7748	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6372	Approved
0.7748	Intermediate Similarity	NPD6373	Approved
0.7739	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6009	Approved
0.7727	Intermediate Similarity	NPD5697	Approved
0.7727	Intermediate Similarity	NPD5701	Approved
0.7699	Intermediate Similarity	NPD8297	Approved
0.7679	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6881	Approved
0.7658	Intermediate Similarity	NPD6899	Approved
0.7658	Intermediate Similarity	NPD6011	Approved
0.7658	Intermediate Similarity	NPD7320	Approved
0.7658	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8328	Phase 3
0.7627	Intermediate Similarity	NPD5983	Phase 2
0.7611	Intermediate Similarity	NPD6649	Approved
0.7611	Intermediate Similarity	NPD6650	Approved
0.7589	Intermediate Similarity	NPD6014	Approved
0.7589	Intermediate Similarity	NPD6012	Approved
0.7589	Intermediate Similarity	NPD6013	Approved
0.7583	Intermediate Similarity	NPD7492	Approved
0.7547	Intermediate Similarity	NPD4697	Phase 3
0.7542	Intermediate Similarity	NPD6054	Approved
0.7542	Intermediate Similarity	NPD6059	Approved
0.7522	Intermediate Similarity	NPD7290	Approved
0.7522	Intermediate Similarity	NPD7102	Approved
0.7522	Intermediate Similarity	NPD6883	Approved
0.7521	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD7604	Phase 2
0.7479	Intermediate Similarity	NPD6015	Approved
0.7479	Intermediate Similarity	NPD6016	Approved
0.7477	Intermediate Similarity	NPD4755	Approved
0.7477	Intermediate Similarity	NPD7902	Approved
0.7459	Intermediate Similarity	NPD8293	Discontinued
0.7459	Intermediate Similarity	NPD7078	Approved
0.7456	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6847	Approved
0.7456	Intermediate Similarity	NPD6617	Approved
0.7456	Intermediate Similarity	NPD8130	Phase 1
0.7456	Intermediate Similarity	NPD6869	Approved
0.7429	Intermediate Similarity	NPD6399	Phase 3
0.7417	Intermediate Similarity	NPD6370	Approved
0.7417	Intermediate Similarity	NPD5988	Approved
0.7411	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5696	Approved
0.7398	Intermediate Similarity	NPD7736	Approved
0.7391	Intermediate Similarity	NPD6882	Approved
0.7383	Intermediate Similarity	NPD5222	Approved
0.7383	Intermediate Similarity	NPD5221	Approved
0.7383	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6336	Discontinued
0.7368	Intermediate Similarity	NPD4634	Approved
0.7358	Intermediate Similarity	NPD7748	Approved
0.7353	Intermediate Similarity	NPD3618	Phase 1
0.7339	Intermediate Similarity	NPD5286	Approved
0.7339	Intermediate Similarity	NPD5285	Approved
0.7339	Intermediate Similarity	NPD4696	Approved
0.7339	Intermediate Similarity	NPD4700	Approved
0.7333	Intermediate Similarity	NPD7515	Phase 2
0.7315	Intermediate Similarity	NPD5173	Approved
0.7308	Intermediate Similarity	NPD5328	Approved
0.7273	Intermediate Similarity	NPD5223	Approved
0.7257	Intermediate Similarity	NPD6412	Phase 2
0.7248	Intermediate Similarity	NPD7638	Approved
0.7248	Intermediate Similarity	NPD4225	Approved
0.7207	Intermediate Similarity	NPD5224	Approved
0.7207	Intermediate Similarity	NPD5225	Approved
0.7207	Intermediate Similarity	NPD5211	Phase 2
0.7207	Intermediate Similarity	NPD4633	Approved
0.7207	Intermediate Similarity	NPD5226	Approved
0.7203	Intermediate Similarity	NPD6274	Approved
0.7196	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7900	Approved
0.719	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7639	Approved
0.7182	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD6079	Approved
0.7156	Intermediate Similarity	NPD6084	Phase 2
0.7156	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD5174	Approved
0.7143	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD5175	Approved
0.712	Intermediate Similarity	NPD6033	Approved
0.7083	Intermediate Similarity	NPD6313	Approved
0.7083	Intermediate Similarity	NPD6335	Approved
0.7083	Intermediate Similarity	NPD6314	Approved
0.708	Intermediate Similarity	NPD5141	Approved
0.7059	Intermediate Similarity	NPD6868	Approved
0.7054	Intermediate Similarity	NPD7632	Discontinued
0.7048	Intermediate Similarity	NPD6672	Approved
0.7048	Intermediate Similarity	NPD5737	Approved
0.7043	Intermediate Similarity	NPD6686	Approved
0.7031	Intermediate Similarity	NPD6845	Suspended
0.7025	Intermediate Similarity	NPD7100	Approved
0.7025	Intermediate Similarity	NPD7101	Approved
0.7018	Intermediate Similarity	NPD4767	Approved
0.7018	Intermediate Similarity	NPD4768	Approved
0.6972	Remote Similarity	NPD5210	Approved
0.6972	Remote Similarity	NPD4629	Approved
0.6972	Remote Similarity	NPD5695	Phase 3
0.6961	Remote Similarity	NPD3667	Approved
0.696	Remote Similarity	NPD7507	Approved
0.6953	Remote Similarity	NPD7260	Phase 2
0.6952	Remote Similarity	NPD3573	Approved
0.6944	Remote Similarity	NPD4202	Approved
0.6911	Remote Similarity	NPD6908	Approved
0.6911	Remote Similarity	NPD6921	Approved
0.6911	Remote Similarity	NPD6909	Approved
0.69	Remote Similarity	NPD3617	Approved
0.6897	Remote Similarity	NPD5128	Approved
0.6897	Remote Similarity	NPD4730	Approved
0.6897	Remote Similarity	NPD4729	Approved
0.6857	Remote Similarity	NPD6409	Approved
0.6857	Remote Similarity	NPD7334	Approved
0.6857	Remote Similarity	NPD5330	Approved
0.6857	Remote Similarity	NPD6684	Approved
0.6857	Remote Similarity	NPD7146	Approved
0.6857	Remote Similarity	NPD7521	Approved
0.6852	Remote Similarity	NPD8035	Phase 2
0.6852	Remote Similarity	NPD8034	Phase 2
0.6827	Remote Similarity	NPD4786	Approved
0.6827	Remote Similarity	NPD3665	Phase 1
0.6827	Remote Similarity	NPD3133	Approved
0.6827	Remote Similarity	NPD3666	Approved
0.6822	Remote Similarity	NPD4753	Phase 2
0.6822	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6067	Discontinued
0.6797	Remote Similarity	NPD7319	Approved
0.678	Remote Similarity	NPD5247	Approved
0.678	Remote Similarity	NPD5248	Approved
0.678	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5251	Approved
0.678	Remote Similarity	NPD5250	Approved
0.678	Remote Similarity	NPD5169	Approved
0.678	Remote Similarity	NPD5249	Phase 3
0.678	Remote Similarity	NPD5135	Approved
0.6765	Remote Similarity	NPD4695	Discontinued
0.6762	Remote Similarity	NPD1694	Approved
0.6752	Remote Similarity	NPD5168	Approved
0.6729	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6903	Approved
0.6727	Remote Similarity	NPD5282	Discontinued
0.6723	Remote Similarity	NPD5216	Approved
0.6723	Remote Similarity	NPD5127	Approved
0.6723	Remote Similarity	NPD5215	Approved
0.6723	Remote Similarity	NPD5217	Approved
0.6698	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5279	Phase 3
0.6697	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6604	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3703	Phase 2
0.6577	Remote Similarity	NPD6001	Approved
0.6569	Remote Similarity	NPD6118	Approved
0.6569	Remote Similarity	NPD6115	Approved
0.6569	Remote Similarity	NPD6114	Approved
0.6569	Remote Similarity	NPD6697	Approved
0.6557	Remote Similarity	NPD5167	Approved
0.6545	Remote Similarity	NPD5284	Approved
0.6545	Remote Similarity	NPD5693	Phase 1
0.6545	Remote Similarity	NPD5281	Approved
0.6529	Remote Similarity	NPD6053	Discontinued
0.6522	Remote Similarity	NPD1700	Approved
0.6519	Remote Similarity	NPD6334	Approved
0.6519	Remote Similarity	NPD6333	Approved
0.6518	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6101	Approved
0.6509	Remote Similarity	NPD4197	Approved
0.6509	Remote Similarity	NPD3668	Phase 3
0.6508	Remote Similarity	NPD8516	Approved
0.6508	Remote Similarity	NPD8515	Approved
0.6508	Remote Similarity	NPD8513	Phase 3
0.6508	Remote Similarity	NPD8517	Approved
0.6486	Remote Similarity	NPD5778	Approved
0.6486	Remote Similarity	NPD5779	Approved
0.648	Remote Similarity	NPD7516	Approved
0.6475	Remote Similarity	NPD8133	Approved
0.6471	Remote Similarity	NPD6116	Phase 1
0.646	Remote Similarity	NPD7614	Phase 1
0.6455	Remote Similarity	NPD46	Approved
0.6455	Remote Similarity	NPD6698	Approved
0.6455	Remote Similarity	NPD5692	Phase 3
0.6449	Remote Similarity	NPD5329	Approved
0.64	Remote Similarity	NPD7328	Approved
0.64	Remote Similarity	NPD7327	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