NPASS Compound

Structure

CID212843 OpenBabel06191716002D 36 38 0 0 1 0 0 0 0 0999 V2000 1.4164 5.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 5.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 3.0032 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 0.8660 -1.5000 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 4.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.3660 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 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 4.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 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 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 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5981 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 4 19 1 0 0 0 0 5 20 2 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 25 1 0 0 0 0 17 31 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 21 10 1 6 0 0 0 21 27 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 6 0 0 0 23 24 2 0 0 0 0 23 29 1 0 0 0 0 24 31 1 0 0 0 0 25 27 1 0 0 0 0 25 32 1 1 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 30 1 6 0 0 0 28 35 2 0 0 0 0 28 36 1 0 0 0 0 29 6 1 6 0 0 0 30 31 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.35
Volume:	549.831
LogP:	5.092
LogD:	2.998
LogS:	-4.369
# Rotatable Bonds:	10
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	5.09
Fsp3:	0.742
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.717
MDCK Permeability:	5.20783987667528e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.58
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	92.31099700927734%
Volume Distribution (VD):	0.453
Pgp-substrate:	2.7719979286193848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.483
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	1.567
Half-life (T1/2):	0.742

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.241
Maximum Recommended Daily Dose:	0.108
Skin Sensitization:	0.037
Carcinogencity:	0.153
Eye Corrosion:	0.007
Eye Irritation:	0.021
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC212843

Natural Product ID:	NPC212843
*Common Name:**	Poricoic Acid H
IUPAC Name:	(2R)-2-[(2R,3R,3aR,6S,7S,9bR)-6-(2-carboxyethyl)-2-hydroxy-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,5,7,8,9-octahydrocyclopenta[a]naphthalen-3-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms:	Poricoic Acid H
Standard InCHIKey:	GKXXWKRLARTIQL-SMFZDKLCSA-N
Standard InCHI:	InChI=1S/C31H48O5/c1-18(2)20(5)9-10-21(28(35)36)27-25(32)17-31(8)24-12-11-22(19(3)4)29(6,15-14-26(33)34)23(24)13-16-30(27,31)7/h18,21-22,25,27,32H,3,5,9-17H2,1-2,4,6-8H3,(H,33,34)(H,35,36)/p-2/t21-,22+,25-,27+,29+,30-,31+/m1/s1
SMILES:	CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2(C)C3=C(CC[C@]12C)[C@@](C)(CCC(=O)[O-])[C@@H](CC3)C(=C)C)O)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251767
PubChem CID:	10918099
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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	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
IC50	10
Others	5

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[471329]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	28400.0	nM	PMID[471330]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	28400.0	nM	PMID[471331]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[471331]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	>	100000.0	nM	PMID[471331]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	100000.0	nM	PMID[471331]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	100000.0	nM	PMID[471331]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	100000.0	nM	PMID[471331]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[471329]
NPT2	Others	Unspecified		Activity	=	15.7	%	PMID[471329]
NPT2	Others	Unspecified		Activity	=	53.8	%	PMID[471329]
NPT2	Others	Unspecified		Activity	=	80.8	%	PMID[471329]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[471330]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[471331]

☑ 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 NPC212843 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	166
0.1-0.2	1239
0.2-0.3	6288
0.3-0.4	15660
0.4-0.5	6733
0.5-0.6	6947
0.6-0.7	4729
0.7-0.8	845
0.8-0.85	56
0.85-0.9	22
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC312215
0.9756	High Similarity	NPC294480
0.9756	High Similarity	NPC183546
0.9639	High Similarity	NPC54689
0.9639	High Similarity	NPC155479
0.9524	High Similarity	NPC46281
0.9518	High Similarity	NPC48866
0.9518	High Similarity	NPC247406
0.9412	High Similarity	NPC23434
0.9302	High Similarity	NPC152897
0.9302	High Similarity	NPC243866
0.9302	High Similarity	NPC66429
0.9294	High Similarity	NPC123854
0.9186	High Similarity	NPC45269
0.9186	High Similarity	NPC154101
0.9091	High Similarity	NPC69548
0.9091	High Similarity	NPC263347
0.9091	High Similarity	NPC162001
0.9091	High Similarity	NPC45324
0.9091	High Similarity	NPC222845
0.9091	High Similarity	NPC184848
0.908	High Similarity	NPC470376
0.908	High Similarity	NPC470375
0.8989	High Similarity	NPC155676
0.8977	High Similarity	NPC7165
0.8876	High Similarity	NPC20546
0.8864	High Similarity	NPC206810
0.8837	High Similarity	NPC242864
0.8824	High Similarity	NPC55309
0.8824	High Similarity	NPC28252
0.881	High Similarity	NPC165064
0.8791	High Similarity	NPC48647
0.8791	High Similarity	NPC477813
0.8791	High Similarity	NPC186810
0.875	High Similarity	NPC150383
0.8736	High Similarity	NPC214387
0.8721	High Similarity	NPC159046
0.8721	High Similarity	NPC233836
0.8721	High Similarity	NPC187376
0.8721	High Similarity	NPC167877
0.8706	High Similarity	NPC474218
0.8681	High Similarity	NPC107243
0.8681	High Similarity	NPC469432
0.8681	High Similarity	NPC57416
0.8667	High Similarity	NPC469599
0.8667	High Similarity	NPC48330
0.8652	High Similarity	NPC25750
0.8636	High Similarity	NPC477147
0.8636	High Similarity	NPC477149
0.8636	High Similarity	NPC469400
0.8605	High Similarity	NPC155011
0.8588	High Similarity	NPC82902
0.8571	High Similarity	NPC173272
0.8571	High Similarity	NPC133391
0.8539	High Similarity	NPC297265
0.8523	High Similarity	NPC77168
0.8523	High Similarity	NPC215029
0.8523	High Similarity	NPC474889
0.8523	High Similarity	NPC102414
0.8523	High Similarity	NPC475921
0.8523	High Similarity	NPC84271
0.8523	High Similarity	NPC476733
0.8523	High Similarity	NPC474704
0.8523	High Similarity	NPC477943
0.8511	High Similarity	NPC195290
0.8511	High Similarity	NPC204450
0.8506	High Similarity	NPC317590
0.8506	High Similarity	NPC142361
0.8506	High Similarity	NPC474684
0.8506	High Similarity	NPC96496
0.8495	Intermediate Similarity	NPC218383
0.8478	Intermediate Similarity	NPC475894
0.8471	Intermediate Similarity	NPC245866
0.8462	Intermediate Similarity	NPC241156
0.8452	Intermediate Similarity	NPC38350
0.8452	Intermediate Similarity	NPC201912
0.8434	Intermediate Similarity	NPC477371
0.8434	Intermediate Similarity	NPC196827
0.8434	Intermediate Similarity	NPC274996
0.8427	Intermediate Similarity	NPC44240
0.8427	Intermediate Similarity	NPC111585
0.8427	Intermediate Similarity	NPC148414
0.8427	Intermediate Similarity	NPC175628
0.8427	Intermediate Similarity	NPC171441
0.8421	Intermediate Similarity	NPC236390
0.8404	Intermediate Similarity	NPC474327
0.8391	Intermediate Similarity	NPC469994
0.8391	Intermediate Similarity	NPC80590
0.8387	Intermediate Similarity	NPC197386
0.8387	Intermediate Similarity	NPC10364
0.8387	Intermediate Similarity	NPC235464
0.8387	Intermediate Similarity	NPC166745
0.8372	Intermediate Similarity	NPC473246
0.8372	Intermediate Similarity	NPC100391
0.837	Intermediate Similarity	NPC125622
0.837	Intermediate Similarity	NPC42042
0.837	Intermediate Similarity	NPC95565
0.8353	Intermediate Similarity	NPC260956
0.8353	Intermediate Similarity	NPC296367
0.8352	Intermediate Similarity	NPC166906
0.8352	Intermediate Similarity	NPC469406
0.8333	Intermediate Similarity	NPC110657
0.8333	Intermediate Similarity	NPC86266
0.8333	Intermediate Similarity	NPC477812
0.8333	Intermediate Similarity	NPC189520
0.8333	Intermediate Similarity	NPC107690
0.8333	Intermediate Similarity	NPC212301
0.8333	Intermediate Similarity	NPC26888
0.8298	Intermediate Similarity	NPC205899
0.8295	Intermediate Similarity	NPC134197
0.828	Intermediate Similarity	NPC18319
0.8276	Intermediate Similarity	NPC474083
0.8261	Intermediate Similarity	NPC174948
0.8261	Intermediate Similarity	NPC469995
0.8261	Intermediate Similarity	NPC470016
0.8261	Intermediate Similarity	NPC318282
0.8261	Intermediate Similarity	NPC173875
0.8261	Intermediate Similarity	NPC317586
0.8256	Intermediate Similarity	NPC83569
0.8256	Intermediate Similarity	NPC477373
0.8256	Intermediate Similarity	NPC470015
0.8256	Intermediate Similarity	NPC310470
0.8256	Intermediate Similarity	NPC69279
0.8256	Intermediate Similarity	NPC168188
0.8242	Intermediate Similarity	NPC470254
0.8242	Intermediate Similarity	NPC470224
0.8242	Intermediate Similarity	NPC141497
0.8242	Intermediate Similarity	NPC107674
0.8242	Intermediate Similarity	NPC472942
0.8242	Intermediate Similarity	NPC170220
0.8235	Intermediate Similarity	NPC147066
0.8235	Intermediate Similarity	NPC477372
0.8229	Intermediate Similarity	NPC140723
0.8222	Intermediate Similarity	NPC69622
0.8222	Intermediate Similarity	NPC289213
0.8222	Intermediate Similarity	NPC471896
0.8222	Intermediate Similarity	NPC320026
0.8202	Intermediate Similarity	NPC328313
0.8202	Intermediate Similarity	NPC183374
0.8202	Intermediate Similarity	NPC470417
0.8202	Intermediate Similarity	NPC28227
0.8202	Intermediate Similarity	NPC211162
0.8182	Intermediate Similarity	NPC94755
0.8182	Intermediate Similarity	NPC72133
0.8172	Intermediate Similarity	NPC328371
0.8172	Intermediate Similarity	NPC96859
0.8172	Intermediate Similarity	NPC328162
0.8172	Intermediate Similarity	NPC472941
0.8172	Intermediate Similarity	NPC456
0.8172	Intermediate Similarity	NPC305483
0.8172	Intermediate Similarity	NPC120708
0.8161	Intermediate Similarity	NPC161423
0.8161	Intermediate Similarity	NPC227064
0.8161	Intermediate Similarity	NPC85774
0.8161	Intermediate Similarity	NPC329043
0.8161	Intermediate Similarity	NPC214043
0.8161	Intermediate Similarity	NPC321187
0.8161	Intermediate Similarity	NPC476038
0.8161	Intermediate Similarity	NPC58841
0.8161	Intermediate Similarity	NPC263974
0.8161	Intermediate Similarity	NPC59453
0.8161	Intermediate Similarity	NPC194937
0.8161	Intermediate Similarity	NPC221758
0.8152	Intermediate Similarity	NPC49670
0.8152	Intermediate Similarity	NPC111015
0.8144	Intermediate Similarity	NPC472227
0.8144	Intermediate Similarity	NPC472228
0.814	Intermediate Similarity	NPC240302
0.814	Intermediate Similarity	NPC170985
0.8125	Intermediate Similarity	NPC473928
0.8125	Intermediate Similarity	NPC56498
0.8111	Intermediate Similarity	NPC116146
0.8111	Intermediate Similarity	NPC128496
0.8111	Intermediate Similarity	NPC474570
0.8111	Intermediate Similarity	NPC474679
0.8111	Intermediate Similarity	NPC76879
0.8111	Intermediate Similarity	NPC24772
0.8111	Intermediate Similarity	NPC2983
0.8111	Intermediate Similarity	NPC310236
0.8105	Intermediate Similarity	NPC316964
0.8105	Intermediate Similarity	NPC51370
0.8105	Intermediate Similarity	NPC476274
0.8105	Intermediate Similarity	NPC287833
0.8095	Intermediate Similarity	NPC321514
0.809	Intermediate Similarity	NPC136548
0.809	Intermediate Similarity	NPC477926
0.809	Intermediate Similarity	NPC90652
0.8085	Intermediate Similarity	NPC320306
0.8085	Intermediate Similarity	NPC43747
0.8068	Intermediate Similarity	NPC123319
0.8068	Intermediate Similarity	NPC283733
0.8068	Intermediate Similarity	NPC94531
0.8068	Intermediate Similarity	NPC471224
0.8068	Intermediate Similarity	NPC329738
0.8068	Intermediate Similarity	NPC311702
0.8065	Intermediate Similarity	NPC472932
0.8065	Intermediate Similarity	NPC255809
0.8065	Intermediate Similarity	NPC37646
0.8046	Intermediate Similarity	NPC477852
0.8046	Intermediate Similarity	NPC476082

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 NPC212843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1884
0.2-0.3	4053
0.3-0.4	2082
0.4-0.5	519
0.5-0.6	186
0.6-0.7	203
0.7-0.8	73
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
0.8444	Intermediate Similarity	NPD6399	Phase 3
0.8333	Intermediate Similarity	NPD5281	Approved
0.8333	Intermediate Similarity	NPD5284	Approved
0.8161	Intermediate Similarity	NPD4786	Approved
0.8161	Intermediate Similarity	NPD3133	Approved
0.8161	Intermediate Similarity	NPD3665	Phase 1
0.8161	Intermediate Similarity	NPD3666	Approved
0.8085	Intermediate Similarity	NPD6083	Phase 2
0.8085	Intermediate Similarity	NPD6084	Phase 2
0.8065	Intermediate Similarity	NPD5695	Phase 3
0.7978	Intermediate Similarity	NPD7146	Approved
0.7978	Intermediate Similarity	NPD7521	Approved
0.7978	Intermediate Similarity	NPD7334	Approved
0.7978	Intermediate Similarity	NPD6409	Approved
0.7978	Intermediate Similarity	NPD6684	Approved
0.7978	Intermediate Similarity	NPD5330	Approved
0.7931	Intermediate Similarity	NPD3667	Approved
0.7912	Intermediate Similarity	NPD4753	Phase 2
0.7879	Intermediate Similarity	NPD7128	Approved
0.7879	Intermediate Similarity	NPD5739	Approved
0.7879	Intermediate Similarity	NPD6675	Approved
0.7879	Intermediate Similarity	NPD6402	Approved
0.7865	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD4202	Approved
0.7822	Intermediate Similarity	NPD6372	Approved
0.7822	Intermediate Similarity	NPD6373	Approved
0.7812	Intermediate Similarity	NPD5696	Approved
0.7802	Intermediate Similarity	NPD6903	Approved
0.7802	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD5279	Phase 3
0.7742	Intermediate Similarity	NPD8034	Phase 2
0.7742	Intermediate Similarity	NPD8035	Phase 2
0.7727	Intermediate Similarity	NPD4221	Approved
0.7727	Intermediate Similarity	NPD4223	Phase 3
0.7723	Intermediate Similarity	NPD6881	Approved
0.7723	Intermediate Similarity	NPD6899	Approved
0.7723	Intermediate Similarity	NPD7320	Approved
0.7717	Intermediate Similarity	NPD5328	Approved
0.7708	Intermediate Similarity	NPD4755	Approved
0.7701	Intermediate Similarity	NPD5368	Approved
0.7684	Intermediate Similarity	NPD5210	Approved
0.7684	Intermediate Similarity	NPD4629	Approved
0.7674	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6650	Approved
0.767	Intermediate Similarity	NPD6649	Approved
0.7667	Intermediate Similarity	NPD5329	Approved
0.764	Intermediate Similarity	NPD4788	Approved
0.764	Intermediate Similarity	NPD5362	Discontinued
0.7624	Intermediate Similarity	NPD5701	Approved
0.7624	Intermediate Similarity	NPD5697	Approved
0.7614	Intermediate Similarity	NPD4692	Approved
0.7614	Intermediate Similarity	NPD4139	Approved
0.7614	Intermediate Similarity	NPD5369	Approved
0.7609	Intermediate Similarity	NPD5737	Approved
0.7609	Intermediate Similarity	NPD6672	Approved
0.7582	Intermediate Similarity	NPD6098	Approved
0.7582	Intermediate Similarity	NPD5690	Phase 2
0.7582	Intermediate Similarity	NPD4694	Approved
0.7582	Intermediate Similarity	NPD5280	Approved
0.7573	Intermediate Similarity	NPD6883	Approved
0.7573	Intermediate Similarity	NPD7102	Approved
0.7573	Intermediate Similarity	NPD7290	Approved
0.7556	Intermediate Similarity	NPD4197	Approved
0.7553	Intermediate Similarity	NPD6050	Approved
0.7553	Intermediate Similarity	NPD6079	Approved
0.7553	Intermediate Similarity	NPD7515	Phase 2
0.7551	Intermediate Similarity	NPD5286	Approved
0.7551	Intermediate Similarity	NPD4700	Approved
0.7551	Intermediate Similarity	NPD5285	Approved
0.7551	Intermediate Similarity	NPD4696	Approved
0.7549	Intermediate Similarity	NPD6011	Approved
0.7528	Intermediate Similarity	NPD4270	Approved
0.7528	Intermediate Similarity	NPD4269	Approved
0.7528	Intermediate Similarity	NPD6435	Approved
0.7527	Intermediate Similarity	NPD6673	Approved
0.7527	Intermediate Similarity	NPD6080	Approved
0.7527	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6617	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6012	Approved
0.7476	Intermediate Similarity	NPD6013	Approved
0.7476	Intermediate Similarity	NPD6014	Approved
0.7475	Intermediate Similarity	NPD5223	Approved
0.7447	Intermediate Similarity	NPD5692	Phase 3
0.7447	Intermediate Similarity	NPD5207	Approved
0.7442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6882	Approved
0.7429	Intermediate Similarity	NPD8297	Approved
0.7423	Intermediate Similarity	NPD4697	Phase 3
0.74	Intermediate Similarity	NPD5225	Approved
0.74	Intermediate Similarity	NPD4633	Approved
0.74	Intermediate Similarity	NPD5211	Phase 2
0.74	Intermediate Similarity	NPD5226	Approved
0.74	Intermediate Similarity	NPD5224	Approved
0.7391	Intermediate Similarity	NPD4688	Approved
0.7391	Intermediate Similarity	NPD4693	Phase 3
0.7391	Intermediate Similarity	NPD4138	Approved
0.7391	Intermediate Similarity	NPD5205	Approved
0.7391	Intermediate Similarity	NPD4690	Approved
0.7391	Intermediate Similarity	NPD4689	Approved
0.7368	Intermediate Similarity	NPD5694	Approved
0.7368	Intermediate Similarity	NPD6411	Approved
0.7363	Intermediate Similarity	NPD3668	Phase 3
0.7356	Intermediate Similarity	NPD6116	Phase 1
0.7347	Intermediate Similarity	NPD7902	Approved
0.7327	Intermediate Similarity	NPD5175	Approved
0.7327	Intermediate Similarity	NPD4754	Approved
0.7327	Intermediate Similarity	NPD5174	Approved
0.7326	Intermediate Similarity	NPD6942	Approved
0.7326	Intermediate Similarity	NPD7339	Approved
0.7303	Intermediate Similarity	NPD4252	Approved
0.7303	Intermediate Similarity	NPD4822	Approved
0.7303	Intermediate Similarity	NPD4819	Approved
0.7303	Intermediate Similarity	NPD4821	Approved
0.7303	Intermediate Similarity	NPD7525	Registered
0.7303	Intermediate Similarity	NPD4820	Approved
0.7283	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5363	Approved
0.7282	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD4271	Approved
0.7273	Intermediate Similarity	NPD4268	Approved
0.7273	Intermediate Similarity	NPD7638	Approved
0.7263	Intermediate Similarity	NPD5785	Approved
0.7255	Intermediate Similarity	NPD5141	Approved
0.7253	Intermediate Similarity	NPD5332	Approved
0.7253	Intermediate Similarity	NPD5331	Approved
0.7245	Intermediate Similarity	NPD5221	Approved
0.7245	Intermediate Similarity	NPD5222	Approved
0.7245	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6117	Approved
0.7234	Intermediate Similarity	NPD5208	Approved
0.7222	Intermediate Similarity	NPD4790	Discontinued
0.7216	Intermediate Similarity	NPD7748	Approved
0.7209	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5786	Approved
0.72	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD7639	Approved
0.7196	Intermediate Similarity	NPD4632	Approved
0.7188	Intermediate Similarity	NPD5693	Phase 1
0.7184	Intermediate Similarity	NPD4767	Approved
0.7184	Intermediate Similarity	NPD4768	Approved
0.7184	Intermediate Similarity	NPD6008	Approved
0.7176	Intermediate Similarity	NPD4243	Approved
0.7172	Intermediate Similarity	NPD5173	Approved
0.7158	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6051	Approved
0.7158	Intermediate Similarity	NPD6101	Approved
0.7111	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4748	Discontinued
0.7103	Intermediate Similarity	NPD6053	Discontinued
0.7091	Intermediate Similarity	NPD6335	Approved
0.7083	Intermediate Similarity	NPD4096	Approved
0.7079	Intermediate Similarity	NPD6118	Approved
0.7079	Intermediate Similarity	NPD6114	Approved
0.7079	Intermediate Similarity	NPD3617	Approved
0.7079	Intermediate Similarity	NPD6697	Approved
0.7079	Intermediate Similarity	NPD6115	Approved
0.7064	Intermediate Similarity	NPD6274	Approved
0.7059	Intermediate Similarity	NPD4244	Approved
0.7059	Intermediate Similarity	NPD4245	Approved
0.7053	Intermediate Similarity	NPD4518	Approved
0.7048	Intermediate Similarity	NPD4729	Approved
0.7048	Intermediate Similarity	NPD4730	Approved
0.7048	Intermediate Similarity	NPD5128	Approved
0.7041	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6001	Approved
0.7041	Intermediate Similarity	NPD7900	Approved
0.7027	Intermediate Similarity	NPD7100	Approved
0.7027	Intermediate Similarity	NPD7101	Approved
0.7011	Intermediate Similarity	NPD4784	Approved
0.7011	Intermediate Similarity	NPD6926	Approved
0.7011	Intermediate Similarity	NPD4785	Approved
0.7011	Intermediate Similarity	NPD6924	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD4195	Approved
0.7	Intermediate Similarity	NPD6317	Approved
0.6979	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5654	Approved
0.6941	Remote Similarity	NPD3698	Phase 2
0.6939	Remote Similarity	NPD5133	Approved
0.6939	Remote Similarity	NPD5779	Approved
0.6939	Remote Similarity	NPD5778	Approved
0.6937	Remote Similarity	NPD6313	Approved
0.6937	Remote Similarity	NPD6314	Approved
0.6932	Remote Similarity	NPD3702	Approved
0.6916	Remote Similarity	NPD5169	Approved
0.6916	Remote Similarity	NPD5135	Approved
0.6916	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5251	Approved
0.6916	Remote Similarity	NPD5247	Approved
0.6916	Remote Similarity	NPD4634	Approved
0.6916	Remote Similarity	NPD5248	Approved
0.6916	Remote Similarity	NPD5249	Phase 3
0.6916	Remote Similarity	NPD5250	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