NPASS Compound

Structure

NPC470015 OpenBabel07101719522D 33 36 0 0 1 0 0 0 0 0999 V2000 -5.1453 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4980 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7852 -5.6132 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4251 -7.3074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1379 -6.1485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 3 18 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 25 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 17 2 1 1 0 0 0 17 21 1 0 0 0 0 18 27 1 0 0 0 0 19 4 1 6 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 20 26 2 0 0 0 0 21 29 1 1 0 0 0 22 28 1 1 0 0 0 23 29 1 1 0 0 0 24 30 2 0 0 0 0 25 26 1 0 0 0 0 25 31 2 0 0 0 0 26 28 1 0 0 0 0 27 32 2 0 0 0 0 27 33 1 0 0 0 0 28 5 1 1 0 0 0 29 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.31
Volume:	497.893
LogP:	4.85
LogD:	3.651
LogS:	-4.62
# Rotatable Bonds:	5
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	5.157
Fsp3:	0.759
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.256
MDCK Permeability:	1.3704727280128282e-05
Pgp-inhibitor:	0.566
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.87
30% Bioavailability (F30%):	0.797

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.519
Plasma Protein Binding (PPB):	94.17974090576172%
Volume Distribution (VD):	0.876
Pgp-substrate:	1.8843207359313965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.469
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.155
CYP2C9-substrate:	0.468
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.441
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	7.236
Half-life (T1/2):	0.369

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.399
Drug-inuced Liver Injury (DILI):	0.579
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.086
Skin Sensitization:	0.097
Carcinogencity:	0.226
Eye Corrosion:	0.1
Eye Irritation:	0.019
Respiratory Toxicity:	0.598

Download Data

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

Natural Product: NPC470015

Natural Product ID:	NPC470015
*Common Name:**	Antcin A
IUPAC Name:	(6R)-2-methyl-3-methylidene-6-[(4S,5S,10S,13R,14R,17R)-4,10,13-trimethyl-3,11-dioxo-2,4,5,6,7,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanoic acid
Synonyms:	Antcin A
Standard InCHIKey:	WTSUWKBKPMVEBO-QMHPZZQYSA-N
Standard InCHI:	InChI=1S/C29H42O4/c1-16(18(3)27(32)33)7-8-17(2)21-11-12-23-20-9-10-22-19(4)24(30)13-14-28(22,5)26(20)25(31)15-29(21,23)6/h17-19,21-23H,1,7-15H2,2-6H3,(H,32,33)/t17-,18?,19+,21-,22+,23+,28+,29-/m1/s1
SMILES:	CC(C(=C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC(=O)C1=C2CC[C@@H]2[C@]1(C)CCC(=O)[C@H]2C)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644793
PubChem CID:	10004121
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738384]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17932820]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891260]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[8594142]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	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
EC50	2
ED50	4
IC50	8

Activity Type	# Activity
Cell Line	9
Individual Protein	1
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	IC50	=	4100.0	nM	PMID[508174]
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	=	13.2	ug ml-1	PMID[508174]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	13.3	ug ml-1	PMID[508174]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[508174]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[508174]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	4900.0	nM	PMID[508175]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	4100.0	nM	PMID[508175]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	45900.0	nM	PMID[508175]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	39400.0	nM	PMID[508176]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	29600.0	nM	PMID[508176]
NPT2	Others	Unspecified		IC50	=	29200.0	nM	PMID[508174]
NPT2	Others	Unspecified		IC50	=	45900.0	nM	PMID[508174]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	10000.0	nM	PMID[508175]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29200.0	nM	PMID[508175]

☑ 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 NPC470015 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	146
0.1-0.2	1083
0.2-0.3	6179
0.3-0.4	15051
0.4-0.5	7676
0.5-0.6	6831
0.6-0.7	4309
0.7-0.8	1155
0.8-0.85	199
0.85-0.9	50
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168188
0.9747	High Similarity	NPC311702
0.9747	High Similarity	NPC123319
0.9747	High Similarity	NPC94531
0.9367	High Similarity	NPC320514
0.9367	High Similarity	NPC327969
0.9367	High Similarity	NPC321289
0.9367	High Similarity	NPC260956
0.9241	High Similarity	NPC38350
0.9241	High Similarity	NPC477372
0.9241	High Similarity	NPC201912
0.9136	High Similarity	NPC320801
0.9136	High Similarity	NPC209882
0.9036	High Similarity	NPC136948
0.9024	High Similarity	NPC29447
0.9024	High Similarity	NPC473038
0.9024	High Similarity	NPC11711
0.9012	High Similarity	NPC69279
0.9012	High Similarity	NPC83569
0.9	High Similarity	NPC147066
0.8987	High Similarity	NPC477371
0.8889	High Similarity	NPC133391
0.8851	High Similarity	NPC166906
0.8846	High Similarity	NPC180886
0.8837	High Similarity	NPC204341
0.8824	High Similarity	NPC262043
0.878	High Similarity	NPC477373
0.8765	High Similarity	NPC278459
0.875	High Similarity	NPC469995
0.875	High Similarity	NPC318282
0.875	High Similarity	NPC317586
0.875	High Similarity	NPC173875
0.875	High Similarity	NPC174948
0.875	High Similarity	NPC470016
0.8706	High Similarity	NPC242864
0.869	High Similarity	NPC222613
0.869	High Similarity	NPC475022
0.869	High Similarity	NPC118648
0.8675	High Similarity	NPC473246
0.8675	High Similarity	NPC164577
0.8659	High Similarity	NPC142253
0.8659	High Similarity	NPC3511
0.8652	High Similarity	NPC305483
0.8652	High Similarity	NPC328162
0.8652	High Similarity	NPC96859
0.8652	High Similarity	NPC328371
0.8625	High Similarity	NPC74410
0.8625	High Similarity	NPC469996
0.8605	High Similarity	NPC214387
0.8605	High Similarity	NPC54689
0.8588	High Similarity	NPC96496
0.8571	High Similarity	NPC469948
0.8571	High Similarity	NPC8571
0.8556	High Similarity	NPC320306
0.8556	High Similarity	NPC43747
0.8554	High Similarity	NPC271784
0.8554	High Similarity	NPC469561
0.8554	High Similarity	NPC97913
0.8539	High Similarity	NPC171395
0.8537	High Similarity	NPC471898
0.8523	High Similarity	NPC206810
0.8523	High Similarity	NPC25750
0.8519	High Similarity	NPC274996
0.8519	High Similarity	NPC472490
0.8519	High Similarity	NPC196827
0.8506	High Similarity	NPC477149
0.8506	High Similarity	NPC477147
0.85	High Similarity	NPC165711
0.8488	Intermediate Similarity	NPC471722
0.8471	Intermediate Similarity	NPC474732
0.8471	Intermediate Similarity	NPC55309
0.8471	Intermediate Similarity	NPC474778
0.8471	Intermediate Similarity	NPC31564
0.8471	Intermediate Similarity	NPC28252
0.8471	Intermediate Similarity	NPC145879
0.8471	Intermediate Similarity	NPC474733
0.8471	Intermediate Similarity	NPC72133
0.8471	Intermediate Similarity	NPC155011
0.8462	Intermediate Similarity	NPC235464
0.8462	Intermediate Similarity	NPC166745
0.8462	Intermediate Similarity	NPC197386
0.8452	Intermediate Similarity	NPC214043
0.8452	Intermediate Similarity	NPC472865
0.8452	Intermediate Similarity	NPC87552
0.8452	Intermediate Similarity	NPC85774
0.8452	Intermediate Similarity	NPC96095
0.8444	Intermediate Similarity	NPC456
0.8444	Intermediate Similarity	NPC472941
0.8434	Intermediate Similarity	NPC472239
0.8434	Intermediate Similarity	NPC193347
0.8415	Intermediate Similarity	NPC26139
0.8409	Intermediate Similarity	NPC26888
0.8391	Intermediate Similarity	NPC474889
0.8391	Intermediate Similarity	NPC1015
0.8391	Intermediate Similarity	NPC474570
0.8391	Intermediate Similarity	NPC31985
0.8375	Intermediate Similarity	NPC246445
0.8372	Intermediate Similarity	NPC159046
0.8372	Intermediate Similarity	NPC233836
0.8372	Intermediate Similarity	NPC58063
0.8372	Intermediate Similarity	NPC475740
0.8372	Intermediate Similarity	NPC187376
0.837	Intermediate Similarity	NPC327431
0.837	Intermediate Similarity	NPC316964
0.8353	Intermediate Similarity	NPC142649
0.8353	Intermediate Similarity	NPC269638
0.8353	Intermediate Similarity	NPC474537
0.8352	Intermediate Similarity	NPC108078
0.8333	Intermediate Similarity	NPC49019
0.8333	Intermediate Similarity	NPC477852
0.8333	Intermediate Similarity	NPC241156
0.8333	Intermediate Similarity	NPC310470
0.8333	Intermediate Similarity	NPC167103
0.8333	Intermediate Similarity	NPC105803
0.8333	Intermediate Similarity	NPC160817
0.8315	Intermediate Similarity	NPC243866
0.8315	Intermediate Similarity	NPC152897
0.8315	Intermediate Similarity	NPC66429
0.8313	Intermediate Similarity	NPC55869
0.8295	Intermediate Similarity	NPC111585
0.8295	Intermediate Similarity	NPC469400
0.8295	Intermediate Similarity	NPC175628
0.8295	Intermediate Similarity	NPC148414
0.8293	Intermediate Similarity	NPC192744
0.8293	Intermediate Similarity	NPC215843
0.8293	Intermediate Similarity	NPC199595
0.8293	Intermediate Similarity	NPC192329
0.8293	Intermediate Similarity	NPC158846
0.828	Intermediate Similarity	NPC163372
0.828	Intermediate Similarity	NPC302537
0.828	Intermediate Similarity	NPC99411
0.8276	Intermediate Similarity	NPC131470
0.8276	Intermediate Similarity	NPC117122
0.8276	Intermediate Similarity	NPC143767
0.8272	Intermediate Similarity	NPC66105
0.8272	Intermediate Similarity	NPC212661
0.8272	Intermediate Similarity	NPC471035
0.8261	Intermediate Similarity	NPC471717
0.8256	Intermediate Similarity	NPC186975
0.8256	Intermediate Similarity	NPC472869
0.8256	Intermediate Similarity	NPC212843
0.8242	Intermediate Similarity	NPC125622
0.8242	Intermediate Similarity	NPC42042
0.8242	Intermediate Similarity	NPC95565
0.8235	Intermediate Similarity	NPC165064
0.8235	Intermediate Similarity	NPC59453
0.8235	Intermediate Similarity	NPC19849
0.8235	Intermediate Similarity	NPC237712
0.8235	Intermediate Similarity	NPC472864
0.8235	Intermediate Similarity	NPC221758
0.8235	Intermediate Similarity	NPC144258
0.8222	Intermediate Similarity	NPC184870
0.8214	Intermediate Similarity	NPC69101
0.8214	Intermediate Similarity	NPC472867
0.8214	Intermediate Similarity	NPC296367
0.8214	Intermediate Similarity	NPC251779
0.8214	Intermediate Similarity	NPC100297
0.8214	Intermediate Similarity	NPC240302
0.8202	Intermediate Similarity	NPC154101
0.8202	Intermediate Similarity	NPC297265
0.8202	Intermediate Similarity	NPC23434
0.8193	Intermediate Similarity	NPC472478
0.8193	Intermediate Similarity	NPC108955
0.8193	Intermediate Similarity	NPC37038
0.8193	Intermediate Similarity	NPC2482
0.8191	Intermediate Similarity	NPC204450
0.8191	Intermediate Similarity	NPC119601
0.8191	Intermediate Similarity	NPC308726
0.8191	Intermediate Similarity	NPC195290
0.8182	Intermediate Similarity	NPC26959
0.8182	Intermediate Similarity	NPC84271
0.8182	Intermediate Similarity	NPC102414
0.8182	Intermediate Similarity	NPC77168
0.8182	Intermediate Similarity	NPC477943
0.8182	Intermediate Similarity	NPC86319
0.8182	Intermediate Similarity	NPC268406
0.8182	Intermediate Similarity	NPC474704
0.8182	Intermediate Similarity	NPC186688
0.8182	Intermediate Similarity	NPC112454
0.8182	Intermediate Similarity	NPC305039
0.8182	Intermediate Similarity	NPC275740
0.8182	Intermediate Similarity	NPC477973
0.8182	Intermediate Similarity	NPC475921
0.8172	Intermediate Similarity	NPC51370
0.8172	Intermediate Similarity	NPC287833
0.8171	Intermediate Similarity	NPC321514
0.8171	Intermediate Similarity	NPC110094
0.8171	Intermediate Similarity	NPC260385
0.8171	Intermediate Similarity	NPC189485
0.8171	Intermediate Similarity	NPC30321
0.8171	Intermediate Similarity	NPC280654
0.8161	Intermediate Similarity	NPC236618
0.8161	Intermediate Similarity	NPC93778
0.8161	Intermediate Similarity	NPC142361
0.8161	Intermediate Similarity	NPC136548
0.8161	Intermediate Similarity	NPC312215
0.8161	Intermediate Similarity	NPC99909
0.8161	Intermediate Similarity	NPC167877
0.8161	Intermediate Similarity	NPC474684
0.8161	Intermediate Similarity	NPC128644

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 NPC470015 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	1486
0.2-0.3	4167
0.3-0.4	2293
0.4-0.5	588
0.5-0.6	185
0.6-0.7	185
0.7-0.8	94
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8621	High Similarity	NPD5284	Approved
0.8621	High Similarity	NPD5281	Approved
0.8434	Intermediate Similarity	NPD4221	Approved
0.8434	Intermediate Similarity	NPD4223	Phase 3
0.8353	Intermediate Similarity	NPD5329	Approved
0.8333	Intermediate Similarity	NPD5695	Phase 3
0.8315	Intermediate Similarity	NPD6399	Phase 3
0.8276	Intermediate Similarity	NPD6672	Approved
0.8276	Intermediate Similarity	NPD5737	Approved
0.8256	Intermediate Similarity	NPD5690	Phase 2
0.8256	Intermediate Similarity	NPD5280	Approved
0.8256	Intermediate Similarity	NPD4694	Approved
0.8235	Intermediate Similarity	NPD4786	Approved
0.8235	Intermediate Similarity	NPD4197	Approved
0.8202	Intermediate Similarity	NPD6050	Approved
0.8182	Intermediate Similarity	NPD6904	Approved
0.8182	Intermediate Similarity	NPD6080	Approved
0.8182	Intermediate Similarity	NPD6673	Approved
0.8182	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3617	Approved
0.8152	Intermediate Similarity	NPD6084	Phase 2
0.8152	Intermediate Similarity	NPD6083	Phase 2
0.8125	Intermediate Similarity	NPD5733	Approved
0.809	Intermediate Similarity	NPD5692	Phase 3
0.8046	Intermediate Similarity	NPD4689	Approved
0.8046	Intermediate Similarity	NPD7146	Approved
0.8046	Intermediate Similarity	NPD4138	Approved
0.8046	Intermediate Similarity	NPD5330	Approved
0.8046	Intermediate Similarity	NPD5279	Phase 3
0.8046	Intermediate Similarity	NPD7334	Approved
0.8046	Intermediate Similarity	NPD4688	Approved
0.8046	Intermediate Similarity	NPD4693	Phase 3
0.8046	Intermediate Similarity	NPD6684	Approved
0.8046	Intermediate Similarity	NPD4690	Approved
0.8046	Intermediate Similarity	NPD5205	Approved
0.8046	Intermediate Similarity	NPD7521	Approved
0.8046	Intermediate Similarity	NPD6409	Approved
0.8023	Intermediate Similarity	NPD3133	Approved
0.8023	Intermediate Similarity	NPD3665	Phase 1
0.8023	Intermediate Similarity	NPD3666	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD5694	Approved
0.7978	Intermediate Similarity	NPD5328	Approved
0.7978	Intermediate Similarity	NPD4753	Phase 2
0.7976	Intermediate Similarity	NPD4695	Discontinued
0.7975	Intermediate Similarity	NPD4747	Approved
0.7901	Intermediate Similarity	NPD4687	Approved
0.7889	Intermediate Similarity	NPD5207	Approved
0.7882	Intermediate Similarity	NPD4692	Approved
0.7882	Intermediate Similarity	NPD4139	Approved
0.7875	Intermediate Similarity	NPD5276	Approved
0.7872	Intermediate Similarity	NPD5696	Approved
0.7865	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD6903	Approved
0.7865	Intermediate Similarity	NPD5208	Approved
0.7848	Intermediate Similarity	NPD4137	Phase 3
0.7841	Intermediate Similarity	NPD6098	Approved
0.7841	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD3618	Phase 1
0.7802	Intermediate Similarity	NPD7515	Phase 2
0.7802	Intermediate Similarity	NPD5693	Phase 1
0.7802	Intermediate Similarity	NPD6079	Approved
0.775	Intermediate Similarity	NPD4691	Approved
0.7742	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4096	Approved
0.7667	Intermediate Similarity	NPD4518	Approved
0.7647	Intermediate Similarity	NPD4195	Approved
0.7634	Intermediate Similarity	NPD7748	Approved
0.7614	Intermediate Similarity	NPD3668	Phase 3
0.7604	Intermediate Similarity	NPD6404	Discontinued
0.7576	Intermediate Similarity	NPD5739	Approved
0.7576	Intermediate Similarity	NPD7128	Approved
0.7576	Intermediate Similarity	NPD6675	Approved
0.7576	Intermediate Similarity	NPD6402	Approved
0.7553	Intermediate Similarity	NPD4629	Approved
0.7553	Intermediate Similarity	NPD5210	Approved
0.7553	Intermediate Similarity	NPD5654	Approved
0.7528	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5133	Approved
0.7527	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD4788	Approved
0.7474	Intermediate Similarity	NPD5221	Approved
0.7474	Intermediate Similarity	NPD5222	Approved
0.7474	Intermediate Similarity	NPD4697	Phase 3
0.7474	Intermediate Similarity	NPD7614	Phase 1
0.7474	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4058	Approved
0.7447	Intermediate Similarity	NPD6001	Approved
0.7444	Intermediate Similarity	NPD4519	Discontinued
0.7444	Intermediate Similarity	NPD4623	Approved
0.7439	Intermediate Similarity	NPD6081	Approved
0.7426	Intermediate Similarity	NPD6899	Approved
0.7426	Intermediate Similarity	NPD7320	Approved
0.7426	Intermediate Similarity	NPD6881	Approved
0.7396	Intermediate Similarity	NPD4755	Approved
0.7396	Intermediate Similarity	NPD5959	Approved
0.7396	Intermediate Similarity	NPD7902	Approved
0.7396	Intermediate Similarity	NPD5173	Approved
0.7353	Intermediate Similarity	NPD6373	Approved
0.7353	Intermediate Similarity	NPD6372	Approved
0.7327	Intermediate Similarity	NPD5701	Approved
0.7327	Intermediate Similarity	NPD5697	Approved
0.7326	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7102	Approved
0.7282	Intermediate Similarity	NPD6883	Approved
0.7282	Intermediate Similarity	NPD7290	Approved
0.7262	Intermediate Similarity	NPD4785	Approved
0.7262	Intermediate Similarity	NPD4784	Approved
0.7255	Intermediate Similarity	NPD6011	Approved
0.725	Intermediate Similarity	NPD4224	Phase 2
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4700	Approved
0.7245	Intermediate Similarity	NPD4696	Approved
0.7234	Intermediate Similarity	NPD8035	Phase 2
0.7234	Intermediate Similarity	NPD8034	Phase 2
0.7229	Intermediate Similarity	NPD4243	Approved
0.7212	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8130	Phase 1
0.7212	Intermediate Similarity	NPD6869	Approved
0.7212	Intermediate Similarity	NPD6617	Approved
0.7212	Intermediate Similarity	NPD6847	Approved
0.7212	Intermediate Similarity	NPD6649	Approved
0.7212	Intermediate Similarity	NPD6650	Approved
0.72	Intermediate Similarity	NPD6052	Approved
0.7184	Intermediate Similarity	NPD6013	Approved
0.7184	Intermediate Similarity	NPD6014	Approved
0.7184	Intermediate Similarity	NPD6012	Approved
0.7176	Intermediate Similarity	NPD6942	Approved
0.7176	Intermediate Similarity	NPD7339	Approved
0.7174	Intermediate Similarity	NPD3573	Approved
0.7172	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD5211	Phase 2
0.71	Intermediate Similarity	NPD5091	Approved
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5224	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.7083	Intermediate Similarity	NPD7900	Approved
0.7083	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7640	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7059	Intermediate Similarity	NPD6008	Approved
0.7053	Intermediate Similarity	NPD6411	Approved
0.7037	Intermediate Similarity	NPD7115	Discovery
0.7037	Intermediate Similarity	NPD7331	Phase 2
0.703	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD5175	Approved
0.703	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6412	Phase 2
0.699	Remote Similarity	NPD6614	Approved
0.6961	Remote Similarity	NPD5141	Approved
0.6957	Remote Similarity	NPD5363	Approved
0.6947	Remote Similarity	NPD5785	Approved
0.6944	Remote Similarity	NPD6868	Approved
0.6939	Remote Similarity	NPD7732	Phase 3
0.6923	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5362	Discontinued
0.6916	Remote Similarity	NPD4632	Approved
0.6914	Remote Similarity	NPD7341	Phase 2
0.6897	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6117	Approved
0.6893	Remote Similarity	NPD4767	Approved
0.6893	Remote Similarity	NPD4768	Approved
0.6889	Remote Similarity	NPD5369	Approved
0.6867	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5360	Phase 3
0.686	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6101	Approved
0.6842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6335	Approved
0.6818	Remote Similarity	NPD6116	Phase 1
0.6813	Remote Similarity	NPD4270	Approved
0.6813	Remote Similarity	NPD4269	Approved
0.6789	Remote Similarity	NPD6274	Approved
0.6782	Remote Similarity	NPD5275	Approved
0.6782	Remote Similarity	NPD4190	Phase 3
0.6778	Remote Similarity	NPD5368	Approved
0.6778	Remote Similarity	NPD7525	Registered
0.6778	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4730	Approved
0.6762	Remote Similarity	NPD5168	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6762	Remote Similarity	NPD5128	Approved
0.6757	Remote Similarity	NPD7100	Approved
0.6757	Remote Similarity	NPD7101	Approved
0.6742	Remote Similarity	NPD6697	Approved
0.6742	Remote Similarity	NPD6118	Approved
0.6742	Remote Similarity	NPD6114	Approved
0.6742	Remote Similarity	NPD6115	Approved
0.6727	Remote Similarity	NPD6009	Approved
0.6727	Remote Similarity	NPD6317	Approved
0.6707	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4789	Approved
0.6701	Remote Similarity	NPD7637	Suspended

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