NPASS Compound

Structure

NPC212812 OpenBabel07101718292D 36 39 0 0 1 0 0 0 0 0999 V2000 -2.7471 4.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7112 3.3549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2112 2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1017 -1.3565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 -1.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6131 1.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5812 0.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6490 3.8549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7471 2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8811 2.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3452 0.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2407 0.1679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4792 1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9459 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6131 3.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6131 2.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0151 2.4888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2112 1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6774 -0.6583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1490 0.9888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4792 4.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3452 3.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3452 2.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2112 2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 -0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4792 2.4888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0151 1.4888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1490 2.9888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0772 0.9888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1774 -1.5243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4792 5.4888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2112 4.4888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3510 3.8549 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 17 1 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 6 0 0 0 19 30 1 0 0 0 0 20 26 1 0 0 0 0 20 31 2 0 0 0 0 21 27 1 0 0 0 0 21 32 2 0 0 0 0 22 29 1 6 0 0 0 22 36 1 0 0 0 0 23 24 1 0 0 0 0 23 33 2 0 0 0 0 24 25 2 0 0 0 0 24 34 1 0 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 27 36 1 0 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 6 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.31
Volume:	532.769
LogP:	3.694
LogD:	2.891
LogS:	-3.1
# Rotatable Bonds:	3
TPSA:	97.74
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.551
Synthetic Accessibility Score:	5.079
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.889
MDCK Permeability:	1.8373852071817964e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.795
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.727
Plasma Protein Binding (PPB):	79.8844223022461%
Volume Distribution (VD):	0.941
Pgp-substrate:	9.26912784576416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.157
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.739

ADMET: Excretion

Clearance (CL):	9.104
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.288
Drug-inuced Liver Injury (DILI):	0.269
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.767
Skin Sensitization:	0.225
Carcinogencity:	0.917
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC212812

Natural Product ID:	NPC212812
*Common Name:**	Sodwanone A
IUPAC Name:	(4aR)-5-[2-[(5aS,6S,7S,9aS)-7-hydroxy-2,2,5a,7-tetramethyl-3-oxo-4,5,6,8,9,9a-hexahydrobenzo[b]oxepin-6-yl]ethyl]-8-hydroxy-1,1,4a,6-tetramethyl-3,4-dihydronaphthalene-2,7-dione
Synonyms:	Sodwanone A
Standard InCHIKey:	JSDOSRZMMGXYIQ-WTFRGCPCSA-N
Standard InCHI:	InChI=1S/C30H44O6/c1-17-18(28(6)14-11-20(31)26(2,3)25(28)24(34)23(17)33)9-10-19-29(7)15-12-21(32)27(4,5)36-22(29)13-16-30(19,8)35/h19,22,34-35H,9-16H2,1-8H3/t19-,22-,28+,29-,30-/m0/s1
SMILES:	CC1=C(CC[C@H]2[C@]3(C)CCC(=O)C(C)(C)O[C@H]3CC[C@]2(C)O)[C@@]2(C)CCC(=O)C(C)(C)C2=C(C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513880
PubChem CID:	21773185
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO32762	axinella cf. bidderi	Species	Axinellidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[12542339]
NPO32762	axinella cf. bidderi	Species	Axinellidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[15043442]
NPO28587	Axinella weltneri	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16124780]
NPO32663	Axinella	Genus	Axinellidae	Eukaryota	n.a.	South African	n.a.	PMID[17190448]
NPO28587	Axinella weltneri	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9249974]
NPO28587	Axinella weltneri	Species	n.a.	n.a.	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	22

Activity Type	# Activity
Cell Line	16
NON-MOLECULAR	3
PROTEIN FAMILY	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	1.8	ug.mL-1	PMID[466444]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	3.8	ug.mL-1	PMID[466444]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[466444]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	7.5	ug.mL-1	PMID[466444]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3.5	ug.mL-1	PMID[466444]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	0.7	ug.mL-1	PMID[466444]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[466444]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	8.5	ug.mL-1	PMID[466444]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.3	ug.mL-1	PMID[466444]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2.1	ug.mL-1	PMID[466444]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2.9	ug.mL-1	PMID[466444]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	3600.0	nM	PMID[466446]
NPT396	Cell Line	T47D	Homo sapiens	IC50	>	30000.0	nM	PMID[466446]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30000.0	nM	PMID[466446]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	30000.0	nM	PMID[466446]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	30000.0	nM	PMID[466446]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.7	ug.mL-1	PMID[466444]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.068	ug.mL-1	PMID[466444]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12000.0	nM	PMID[466445]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	30000.0	nM	PMID[466446]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	20000.0	nM	PMID[466446]

☑ 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 NPC212812 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	232
0.1-0.2	1641
0.2-0.3	5686
0.3-0.4	11329
0.4-0.5	11758
0.5-0.6	7155
0.6-0.7	4292
0.7-0.8	580
0.8-0.85	16
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC248913
0.9205	High Similarity	NPC475001
0.9205	High Similarity	NPC185059
0.8913	High Similarity	NPC293086
0.871	High Similarity	NPC477439
0.8617	High Similarity	NPC477438
0.8617	High Similarity	NPC477437
0.8602	High Similarity	NPC477436
0.8602	High Similarity	NPC477435
0.8485	Intermediate Similarity	NPC40170
0.8333	Intermediate Similarity	NPC91439
0.8265	Intermediate Similarity	NPC46761
0.8242	Intermediate Similarity	NPC197823
0.82	Intermediate Similarity	NPC179208
0.82	Intermediate Similarity	NPC194323
0.8191	Intermediate Similarity	NPC475823
0.8191	Intermediate Similarity	NPC474209
0.8172	Intermediate Similarity	NPC230387
0.8105	Intermediate Similarity	NPC99380
0.8081	Intermediate Similarity	NPC472972
0.8068	Intermediate Similarity	NPC476808
0.8061	Intermediate Similarity	NPC470834
0.802	Intermediate Similarity	NPC470839
0.8	Intermediate Similarity	NPC113393
0.8	Intermediate Similarity	NPC223093
0.7959	Intermediate Similarity	NPC272411
0.7938	Intermediate Similarity	NPC23170
0.7938	Intermediate Similarity	NPC472977
0.7938	Intermediate Similarity	NPC160413
0.7938	Intermediate Similarity	NPC472976
0.7938	Intermediate Similarity	NPC474328
0.7925	Intermediate Similarity	NPC90769
0.7921	Intermediate Similarity	NPC80781
0.7917	Intermediate Similarity	NPC168027
0.7917	Intermediate Similarity	NPC185936
0.7917	Intermediate Similarity	NPC472978
0.7917	Intermediate Similarity	NPC472975
0.7912	Intermediate Similarity	NPC48362
0.7895	Intermediate Similarity	NPC250592
0.7895	Intermediate Similarity	NPC77263
0.7895	Intermediate Similarity	NPC472973
0.7879	Intermediate Similarity	NPC18509
0.7864	Intermediate Similarity	NPC85529
0.7864	Intermediate Similarity	NPC32006
0.7857	Intermediate Similarity	NPC474602
0.7857	Intermediate Similarity	NPC473170
0.7857	Intermediate Similarity	NPC134067
0.7849	Intermediate Similarity	NPC241512
0.7849	Intermediate Similarity	NPC478245
0.7849	Intermediate Similarity	NPC6185
0.7843	Intermediate Similarity	NPC90177
0.7843	Intermediate Similarity	NPC33973
0.7843	Intermediate Similarity	NPC70967
0.7835	Intermediate Similarity	NPC211230
0.7822	Intermediate Similarity	NPC470184
0.7822	Intermediate Similarity	NPC124211
0.781	Intermediate Similarity	NPC20192
0.7789	Intermediate Similarity	NPC307298
0.7788	Intermediate Similarity	NPC44063
0.7778	Intermediate Similarity	NPC96859
0.7778	Intermediate Similarity	NPC328162
0.7778	Intermediate Similarity	NPC305483
0.7767	Intermediate Similarity	NPC2436
0.7767	Intermediate Similarity	NPC65523
0.7767	Intermediate Similarity	NPC135854
0.7767	Intermediate Similarity	NPC470251
0.7767	Intermediate Similarity	NPC213366
0.7767	Intermediate Similarity	NPC216245
0.7767	Intermediate Similarity	NPC137657
0.7757	Intermediate Similarity	NPC474516
0.7757	Intermediate Similarity	NPC193948
0.7755	Intermediate Similarity	NPC245972
0.7755	Intermediate Similarity	NPC196485
0.7755	Intermediate Similarity	NPC103527
0.7745	Intermediate Similarity	NPC308726
0.7745	Intermediate Similarity	NPC119601
0.7745	Intermediate Similarity	NPC53222
0.7745	Intermediate Similarity	NPC470840
0.7742	Intermediate Similarity	NPC251170
0.7742	Intermediate Similarity	NPC40687
0.7732	Intermediate Similarity	NPC111883
0.7732	Intermediate Similarity	NPC73457
0.7732	Intermediate Similarity	NPC155304
0.7723	Intermediate Similarity	NPC88198
0.7723	Intermediate Similarity	NPC144956
0.7708	Intermediate Similarity	NPC474245
0.7708	Intermediate Similarity	NPC68148
0.7708	Intermediate Similarity	NPC65615
0.77	Intermediate Similarity	NPC254496
0.77	Intermediate Similarity	NPC272451
0.77	Intermediate Similarity	NPC273269
0.77	Intermediate Similarity	NPC285513
0.77	Intermediate Similarity	NPC473456
0.7692	Intermediate Similarity	NPC181357
0.7692	Intermediate Similarity	NPC478052
0.7692	Intermediate Similarity	NPC472645
0.7684	Intermediate Similarity	NPC220930
0.7684	Intermediate Similarity	NPC272039
0.7677	Intermediate Similarity	NPC317586
0.7677	Intermediate Similarity	NPC200702
0.7677	Intermediate Similarity	NPC470016
0.7677	Intermediate Similarity	NPC139570
0.767	Intermediate Similarity	NPC131366
0.767	Intermediate Similarity	NPC275583
0.7667	Intermediate Similarity	NPC30321
0.7664	Intermediate Similarity	NPC43775
0.7664	Intermediate Similarity	NPC146945
0.7664	Intermediate Similarity	NPC171888
0.766	Intermediate Similarity	NPC8518
0.766	Intermediate Similarity	NPC470574
0.766	Intermediate Similarity	NPC263997
0.766	Intermediate Similarity	NPC132228
0.766	Intermediate Similarity	NPC474680
0.7653	Intermediate Similarity	NPC79117
0.7653	Intermediate Similarity	NPC271652
0.7647	Intermediate Similarity	NPC472643
0.7647	Intermediate Similarity	NPC302537
0.7647	Intermediate Similarity	NPC163372
0.7647	Intermediate Similarity	NPC469327
0.7642	Intermediate Similarity	NPC2766
0.7642	Intermediate Similarity	NPC87335
0.7642	Intermediate Similarity	NPC27814
0.764	Intermediate Similarity	NPC92080
0.7634	Intermediate Similarity	NPC64600
0.7629	Intermediate Similarity	NPC134321
0.7629	Intermediate Similarity	NPC128672
0.7629	Intermediate Similarity	NPC472325
0.7619	Intermediate Similarity	NPC202524
0.7619	Intermediate Similarity	NPC3316
0.7619	Intermediate Similarity	NPC144854
0.7615	Intermediate Similarity	NPC473798
0.7615	Intermediate Similarity	NPC247069
0.7604	Intermediate Similarity	NPC472802
0.7604	Intermediate Similarity	NPC328539
0.7604	Intermediate Similarity	NPC158778
0.7604	Intermediate Similarity	NPC143767
0.7604	Intermediate Similarity	NPC131470
0.76	Intermediate Similarity	NPC192428
0.76	Intermediate Similarity	NPC157113
0.76	Intermediate Similarity	NPC62516
0.76	Intermediate Similarity	NPC260223
0.7596	Intermediate Similarity	NPC118911
0.7593	Intermediate Similarity	NPC234042
0.7593	Intermediate Similarity	NPC152117
0.7582	Intermediate Similarity	NPC475681
0.7582	Intermediate Similarity	NPC192329
0.7579	Intermediate Similarity	NPC34190
0.7579	Intermediate Similarity	NPC94666
0.7579	Intermediate Similarity	NPC158393
0.7579	Intermediate Similarity	NPC73038
0.7576	Intermediate Similarity	NPC74751
0.7576	Intermediate Similarity	NPC166906
0.7576	Intermediate Similarity	NPC169751
0.7576	Intermediate Similarity	NPC272635
0.7576	Intermediate Similarity	NPC240617
0.7573	Intermediate Similarity	NPC163249
0.7573	Intermediate Similarity	NPC136289
0.757	Intermediate Similarity	NPC473036
0.757	Intermediate Similarity	NPC272898
0.7551	Intermediate Similarity	NPC26865
0.7551	Intermediate Similarity	NPC473166
0.7551	Intermediate Similarity	NPC235704
0.7549	Intermediate Similarity	NPC15390
0.7549	Intermediate Similarity	NPC157787
0.7549	Intermediate Similarity	NPC112167
0.7547	Intermediate Similarity	NPC192813
0.7547	Intermediate Similarity	NPC293850
0.7547	Intermediate Similarity	NPC277017
0.7547	Intermediate Similarity	NPC94942
0.7547	Intermediate Similarity	NPC154608
0.7545	Intermediate Similarity	NPC235539
0.7545	Intermediate Similarity	NPC152199
0.7545	Intermediate Similarity	NPC96312
0.7545	Intermediate Similarity	NPC16081
0.7545	Intermediate Similarity	NPC173686
0.7545	Intermediate Similarity	NPC328374
0.7545	Intermediate Similarity	NPC251236
0.7545	Intermediate Similarity	NPC40632
0.7545	Intermediate Similarity	NPC134869
0.7527	Intermediate Similarity	NPC103486
0.7526	Intermediate Similarity	NPC1015
0.7526	Intermediate Similarity	NPC31985
0.7526	Intermediate Similarity	NPC275740
0.7526	Intermediate Similarity	NPC86319
0.7525	Intermediate Similarity	NPC170131
0.7525	Intermediate Similarity	NPC175351
0.7525	Intermediate Similarity	NPC121402
0.7525	Intermediate Similarity	NPC132753
0.7525	Intermediate Similarity	NPC151681
0.7525	Intermediate Similarity	NPC224356
0.7525	Intermediate Similarity	NPC216904
0.7525	Intermediate Similarity	NPC84335
0.7525	Intermediate Similarity	NPC43747
0.7525	Intermediate Similarity	NPC23680
0.7525	Intermediate Similarity	NPC38530
0.7523	Intermediate Similarity	NPC198539
0.7523	Intermediate Similarity	NPC7921
0.7523	Intermediate Similarity	NPC208998
0.75	Intermediate Similarity	NPC316215
0.75	Intermediate Similarity	NPC475740

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 NPC212812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	2037
0.2-0.3	3992
0.3-0.4	1958
0.4-0.5	565
0.5-0.6	177
0.6-0.7	134
0.7-0.8	65
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8039	Intermediate Similarity	NPD6402	Approved
0.8039	Intermediate Similarity	NPD7128	Approved
0.8039	Intermediate Similarity	NPD5739	Approved
0.8039	Intermediate Similarity	NPD6675	Approved
0.7885	Intermediate Similarity	NPD6899	Approved
0.7885	Intermediate Similarity	NPD7320	Approved
0.7885	Intermediate Similarity	NPD6881	Approved
0.7879	Intermediate Similarity	NPD4755	Approved
0.781	Intermediate Similarity	NPD6373	Approved
0.781	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD5697	Approved
0.7788	Intermediate Similarity	NPD5701	Approved
0.7736	Intermediate Similarity	NPD6883	Approved
0.7736	Intermediate Similarity	NPD7102	Approved
0.7736	Intermediate Similarity	NPD7290	Approved
0.7723	Intermediate Similarity	NPD4696	Approved
0.7723	Intermediate Similarity	NPD5286	Approved
0.7723	Intermediate Similarity	NPD4700	Approved
0.7723	Intermediate Similarity	NPD5285	Approved
0.7714	Intermediate Similarity	NPD6011	Approved
0.7708	Intermediate Similarity	NPD5328	Approved
0.7692	Intermediate Similarity	NPD4695	Discontinued
0.7664	Intermediate Similarity	NPD6847	Approved
0.7664	Intermediate Similarity	NPD6617	Approved
0.7664	Intermediate Similarity	NPD6650	Approved
0.7664	Intermediate Similarity	NPD6649	Approved
0.7664	Intermediate Similarity	NPD6869	Approved
0.7664	Intermediate Similarity	NPD8130	Phase 1
0.7664	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5223	Approved
0.7642	Intermediate Similarity	NPD6014	Approved
0.7642	Intermediate Similarity	NPD6012	Approved
0.7642	Intermediate Similarity	NPD6013	Approved
0.76	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5222	Approved
0.76	Intermediate Similarity	NPD5221	Approved
0.76	Intermediate Similarity	NPD4697	Phase 3
0.7593	Intermediate Similarity	NPD6882	Approved
0.7593	Intermediate Similarity	NPD8297	Approved
0.7576	Intermediate Similarity	NPD7748	Approved
0.7573	Intermediate Similarity	NPD5211	Phase 2
0.7573	Intermediate Similarity	NPD5225	Approved
0.7573	Intermediate Similarity	NPD5226	Approved
0.7573	Intermediate Similarity	NPD4633	Approved
0.7573	Intermediate Similarity	NPD5224	Approved
0.7551	Intermediate Similarity	NPD6079	Approved
0.7525	Intermediate Similarity	NPD5173	Approved
0.7525	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD4754	Approved
0.7473	Intermediate Similarity	NPD3617	Approved
0.7429	Intermediate Similarity	NPD5141	Approved
0.7396	Intermediate Similarity	NPD3618	Phase 1
0.7374	Intermediate Similarity	NPD7515	Phase 2
0.7358	Intermediate Similarity	NPD4768	Approved
0.7358	Intermediate Similarity	NPD4767	Approved
0.7353	Intermediate Similarity	NPD6083	Phase 2
0.7353	Intermediate Similarity	NPD6084	Phase 2
0.73	Intermediate Similarity	NPD6399	Phase 3
0.73	Intermediate Similarity	NPD4202	Approved
0.7257	Intermediate Similarity	NPD6335	Approved
0.7245	Intermediate Similarity	NPD6672	Approved
0.7245	Intermediate Similarity	NPD5737	Approved
0.7232	Intermediate Similarity	NPD6274	Approved
0.7228	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7900	Approved
0.7222	Intermediate Similarity	NPD5128	Approved
0.7222	Intermediate Similarity	NPD4730	Approved
0.7222	Intermediate Similarity	NPD4729	Approved
0.7193	Intermediate Similarity	NPD7100	Approved
0.7193	Intermediate Similarity	NPD7101	Approved
0.7188	Intermediate Similarity	NPD4786	Approved
0.7172	Intermediate Similarity	NPD4753	Phase 2
0.7172	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6317	Approved
0.7158	Intermediate Similarity	NPD3667	Approved
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD3573	Approved
0.713	Intermediate Similarity	NPD6059	Approved
0.713	Intermediate Similarity	NPD6054	Approved
0.7115	Intermediate Similarity	NPD5696	Approved
0.7113	Intermediate Similarity	NPD5329	Approved
0.7105	Intermediate Similarity	NPD6314	Approved
0.7105	Intermediate Similarity	NPD6313	Approved
0.7091	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4634	Approved
0.7091	Intermediate Similarity	NPD5135	Approved
0.7091	Intermediate Similarity	NPD5169	Approved
0.7091	Intermediate Similarity	NPD5249	Phase 3
0.7091	Intermediate Similarity	NPD5247	Approved
0.7091	Intermediate Similarity	NPD5248	Approved
0.7091	Intermediate Similarity	NPD5251	Approved
0.7091	Intermediate Similarity	NPD5250	Approved
0.708	Intermediate Similarity	NPD6868	Approved
0.7069	Intermediate Similarity	NPD6908	Approved
0.7069	Intermediate Similarity	NPD6909	Approved
0.7054	Intermediate Similarity	NPD4632	Approved
0.7041	Intermediate Similarity	NPD5279	Phase 3
0.7041	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6008	Approved
0.7027	Intermediate Similarity	NPD5216	Approved
0.7027	Intermediate Similarity	NPD5217	Approved
0.7027	Intermediate Similarity	NPD5127	Approved
0.7027	Intermediate Similarity	NPD5215	Approved
0.7018	Intermediate Similarity	NPD6009	Approved
0.701	Intermediate Similarity	NPD4197	Approved
0.701	Intermediate Similarity	NPD3666	Approved
0.701	Intermediate Similarity	NPD3665	Phase 1
0.701	Intermediate Similarity	NPD3133	Approved
0.7009	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6904	Approved
0.6983	Remote Similarity	NPD6319	Approved
0.6949	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD6016	Approved
0.6923	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD6015	Approved
0.6909	Remote Similarity	NPD5168	Approved
0.6897	Remote Similarity	NPD7341	Phase 2
0.6891	Remote Similarity	NPD7492	Approved
0.687	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7146	Approved
0.6869	Remote Similarity	NPD5330	Approved
0.6869	Remote Similarity	NPD7521	Approved
0.6869	Remote Similarity	NPD6684	Approved
0.6869	Remote Similarity	NPD6409	Approved
0.6869	Remote Similarity	NPD7334	Approved
0.6864	Remote Similarity	NPD5988	Approved
0.6863	Remote Similarity	NPD6411	Approved
0.6847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5167	Approved
0.6837	Remote Similarity	NPD3668	Phase 3
0.6833	Remote Similarity	NPD6336	Discontinued
0.6833	Remote Similarity	NPD6616	Approved
0.6827	Remote Similarity	NPD4629	Approved
0.6827	Remote Similarity	NPD5210	Approved
0.6807	Remote Similarity	NPD8328	Phase 3
0.6804	Remote Similarity	NPD4221	Approved
0.6804	Remote Similarity	NPD4223	Phase 3
0.6786	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8293	Discontinued
0.6777	Remote Similarity	NPD7078	Approved
0.6771	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6903	Approved
0.6731	Remote Similarity	NPD5282	Discontinued
0.6721	Remote Similarity	NPD6033	Approved
0.6721	Remote Similarity	NPD7736	Approved
0.67	Remote Similarity	NPD5280	Approved
0.67	Remote Similarity	NPD4694	Approved
0.67	Remote Similarity	NPD5690	Phase 2
0.67	Remote Similarity	NPD6098	Approved
0.6699	Remote Similarity	NPD5693	Phase 1
0.6699	Remote Similarity	NPD6050	Approved
0.6699	Remote Similarity	NPD8034	Phase 2
0.6699	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD7638	Approved
0.6629	Remote Similarity	NPD3704	Approved
0.6602	Remote Similarity	NPD5692	Phase 3
0.6598	Remote Similarity	NPD7525	Registered
0.6581	Remote Similarity	NPD7115	Discovery
0.6574	Remote Similarity	NPD7639	Approved
0.6574	Remote Similarity	NPD7640	Approved
0.6566	Remote Similarity	NPD4788	Approved
0.6549	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5694	Approved
0.6535	Remote Similarity	NPD4693	Phase 3
0.6535	Remote Similarity	NPD4519	Discontinued
0.6535	Remote Similarity	NPD4689	Approved
0.6535	Remote Similarity	NPD4688	Approved
0.6535	Remote Similarity	NPD4623	Approved
0.6535	Remote Similarity	NPD5205	Approved
0.6535	Remote Similarity	NPD4690	Approved
0.6535	Remote Similarity	NPD4138	Approved
0.6522	Remote Similarity	NPD6053	Discontinued
0.6518	Remote Similarity	NPD6412	Phase 2
0.6518	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7645	Phase 2
0.6455	Remote Similarity	NPD7632	Discontinued
0.6444	Remote Similarity	NPD7331	Phase 2
0.6436	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1696	Phase 3
0.6421	Remote Similarity	NPD3703	Phase 2
0.6381	Remote Similarity	NPD5284	Approved
0.6381	Remote Similarity	NPD5281	Approved
0.6364	Remote Similarity	NPD4139	Approved
0.6364	Remote Similarity	NPD4692	Approved
0.6355	Remote Similarity	NPD5654	Approved
0.633	Remote Similarity	NPD4225	Approved
0.6321	Remote Similarity	NPD5133	Approved
0.6321	Remote Similarity	NPD5778	Approved
0.6321	Remote Similarity	NPD5779	Approved
0.63	Remote Similarity	NPD4752	Clinical (unspecified phase)

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