NPASS Compound

Structure

CID302360 OpenBabel06191716112D 25 26 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -3.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 1 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 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 7 2 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 22 1 0 0 0 0 12 15 2 0 0 0 0 13 1 1 1 0 0 0 13 21 1 0 0 0 0 15 20 1 0 0 0 0 16 6 1 1 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 6 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.21
Volume:	376.638
LogP:	2.465
LogD:	1.477
LogS:	-2.871
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	5.036
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.186
MDCK Permeability:	5.158851490705274e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.91
20% Bioavailability (F20%):	0.127
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	94.36181640625%
Volume Distribution (VD):	0.364
Pgp-substrate:	4.47214937210083%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.677
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	1.933
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.556
Drug-inuced Liver Injury (DILI):	0.682
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.784
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.882
Carcinogencity:	0.105
Eye Corrosion:	0.008
Eye Irritation:	0.03
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC302360

Natural Product ID:	NPC302360
*Common Name:**	Carneic Acid B
IUPAC Name:	(2E,4E)-5-[(1R,2R,4aS,5R,8R,8aR)-5-hydroxy-2-[(E)-4-hydroxybut-2-en-2-yl]-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]penta-2,4-dienoic acid
Synonyms:	Carneic acid B
Standard InCHIKey:	YGIXVFNOSSPFLR-RYAGCBDWSA-N
Standard InCHI:	InChI=1S/C21H30O4/c1-13-8-9-18(23)17-12-15(3)20(14(2)10-11-22)16(21(13)17)6-4-5-7-19(24)25/h4-7,10,12-13,16-18,20-23H,8-9,11H2,1-3H3,(H,24,25)/b6-4+,7-5+,14-10+/t13-,16+,17+,18-,20+,21-/m1/s1
SMILES:	C[C@@H]1CC[C@H]([C@@H]2C=C(C)[C@H](/C(=C/CO)/C)[C@H](/C=C/C=C/C(=O)O)[C@@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498066
PubChem CID:	16083153
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0003086] Medium-chain fatty acids

*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
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	stem	n.a.	PMID[12560039]
NPO28797	Hypoxylon carneum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933875]
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9463	Eschenbachia blinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9463	Eschenbachia blinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3596	Podocarpus milanjianus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25288	Planchonia careya	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23823	Tessaria fastigiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23528	Senecio swaziensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25781	Cassinia uncata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25562	Cephaelis correae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28797	Hypoxylon carneum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25413	Polyporus benzoinus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23262	Lonicera xylosteum	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9463	Eschenbachia blinii	Species	Asteraceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[575597]
NPT3480	Organism	Yarrowia lipolytica	Yarrowia lipolytica	MIC	=	25.0	ug.mL-1	PMID[575597]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	=	12.5	ug.mL-1	PMID[575597]
NPT3482	Organism	Penicillium griseofulvum	Penicillium griseofulvum	MIC	=	25.0	ug.mL-1	PMID[575597]
NPT3483	Organism	Stachybotrys chartarum	Stachybotrys chartarum	MIC	=	25.0	ug.mL-1	PMID[575597]
NPT3484	Organism	Hypocrea lixii	Hypocrea lixii	MIC	=	50.0	ug.mL-1	PMID[575597]

☑ 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 NPC302360 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	163
0.1-0.2	898
0.2-0.3	3950
0.3-0.4	9207
0.4-0.5	14961
0.5-0.6	7976
0.6-0.7	4437
0.7-0.8	1020
0.8-0.85	57
0.85-0.9	13
0.9-0.95	6
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC57370
0.9512	High Similarity	NPC7280
0.9512	High Similarity	NPC229612
0.9383	High Similarity	NPC109528
0.925	High Similarity	NPC224455
0.8902	High Similarity	NPC79945
0.8721	High Similarity	NPC314727
0.8667	High Similarity	NPC99726
0.8659	High Similarity	NPC159148
0.8636	High Similarity	NPC214697
0.8554	High Similarity	NPC2524
0.8554	High Similarity	NPC256112
0.8537	High Similarity	NPC281880
0.8523	High Similarity	NPC212948
0.8462	Intermediate Similarity	NPC141401
0.8427	Intermediate Similarity	NPC205034
0.8427	Intermediate Similarity	NPC152778
0.8427	Intermediate Similarity	NPC162615
0.8409	Intermediate Similarity	NPC182136
0.8409	Intermediate Similarity	NPC310479
0.8372	Intermediate Similarity	NPC475069
0.8372	Intermediate Similarity	NPC175145
0.8372	Intermediate Similarity	NPC473226
0.8352	Intermediate Similarity	NPC473153
0.8352	Intermediate Similarity	NPC250757
0.8352	Intermediate Similarity	NPC190713
0.8352	Intermediate Similarity	NPC301534
0.8333	Intermediate Similarity	NPC279410
0.8333	Intermediate Similarity	NPC119562
0.8333	Intermediate Similarity	NPC191521
0.8295	Intermediate Similarity	NPC16265
0.8295	Intermediate Similarity	NPC262858
0.8295	Intermediate Similarity	NPC146554
0.8295	Intermediate Similarity	NPC118011
0.8295	Intermediate Similarity	NPC36668
0.8295	Intermediate Similarity	NPC472240
0.8235	Intermediate Similarity	NPC476927
0.8214	Intermediate Similarity	NPC170303
0.8202	Intermediate Similarity	NPC221111
0.8202	Intermediate Similarity	NPC280149
0.8202	Intermediate Similarity	NPC78973
0.8182	Intermediate Similarity	NPC104560
0.8182	Intermediate Similarity	NPC473229
0.8161	Intermediate Similarity	NPC82979
0.8152	Intermediate Similarity	NPC16967
0.8132	Intermediate Similarity	NPC470255
0.8132	Intermediate Similarity	NPC476186
0.8125	Intermediate Similarity	NPC265485
0.8125	Intermediate Similarity	NPC220939
0.8095	Intermediate Similarity	NPC271104
0.8085	Intermediate Similarity	NPC266955
0.8072	Intermediate Similarity	NPC172066
0.8068	Intermediate Similarity	NPC245004
0.8049	Intermediate Similarity	NPC265588
0.8046	Intermediate Similarity	NPC35933
0.8023	Intermediate Similarity	NPC52108
0.8023	Intermediate Similarity	NPC474789
0.8022	Intermediate Similarity	NPC476304
0.8022	Intermediate Similarity	NPC38232
0.8	Intermediate Similarity	NPC6663
0.8	Intermediate Similarity	NPC115899
0.8	Intermediate Similarity	NPC142163
0.8	Intermediate Similarity	NPC473420
0.8	Intermediate Similarity	NPC23954
0.8	Intermediate Similarity	NPC282524
0.7979	Intermediate Similarity	NPC478056
0.7979	Intermediate Similarity	NPC108368
0.7979	Intermediate Similarity	NPC57079
0.7979	Intermediate Similarity	NPC474440
0.7979	Intermediate Similarity	NPC92275
0.7955	Intermediate Similarity	NPC131813
0.7952	Intermediate Similarity	NPC91594
0.7952	Intermediate Similarity	NPC283619
0.7952	Intermediate Similarity	NPC132542
0.7935	Intermediate Similarity	NPC469491
0.7935	Intermediate Similarity	NPC474690
0.7935	Intermediate Similarity	NPC469406
0.7935	Intermediate Similarity	NPC299100
0.7935	Intermediate Similarity	NPC57117
0.7931	Intermediate Similarity	NPC306951
0.7912	Intermediate Similarity	NPC110923
0.7912	Intermediate Similarity	NPC142838
0.7912	Intermediate Similarity	NPC472811
0.7912	Intermediate Similarity	NPC72845
0.7912	Intermediate Similarity	NPC74296
0.7889	Intermediate Similarity	NPC246028
0.7889	Intermediate Similarity	NPC472983
0.7889	Intermediate Similarity	NPC20946
0.7889	Intermediate Similarity	NPC50488
0.7889	Intermediate Similarity	NPC474396
0.7889	Intermediate Similarity	NPC82876
0.7879	Intermediate Similarity	NPC470024
0.7865	Intermediate Similarity	NPC181327
0.7865	Intermediate Similarity	NPC131329
0.7857	Intermediate Similarity	NPC172867
0.7849	Intermediate Similarity	NPC183012
0.7849	Intermediate Similarity	NPC180950
0.7835	Intermediate Similarity	NPC475050
0.7835	Intermediate Similarity	NPC85742
0.7831	Intermediate Similarity	NPC250621
0.7826	Intermediate Similarity	NPC472812
0.7826	Intermediate Similarity	NPC53555
0.7821	Intermediate Similarity	NPC202017
0.7821	Intermediate Similarity	NPC255781
0.7816	Intermediate Similarity	NPC297398
0.7812	Intermediate Similarity	NPC115862
0.7791	Intermediate Similarity	NPC476646
0.7789	Intermediate Similarity	NPC235464
0.7789	Intermediate Similarity	NPC218107
0.7789	Intermediate Similarity	NPC316598
0.7789	Intermediate Similarity	NPC471717
0.7789	Intermediate Similarity	NPC166745
0.7778	Intermediate Similarity	NPC291665
0.7778	Intermediate Similarity	NPC48107
0.7778	Intermediate Similarity	NPC95863
0.7778	Intermediate Similarity	NPC249889
0.7778	Intermediate Similarity	NPC109376
0.7778	Intermediate Similarity	NPC193843
0.7766	Intermediate Similarity	NPC195366
0.7766	Intermediate Similarity	NPC114743
0.7765	Intermediate Similarity	NPC470429
0.7765	Intermediate Similarity	NPC242767
0.7765	Intermediate Similarity	NPC100906
0.7753	Intermediate Similarity	NPC472974
0.7753	Intermediate Similarity	NPC474970
0.7742	Intermediate Similarity	NPC477129
0.7742	Intermediate Similarity	NPC474922
0.7742	Intermediate Similarity	NPC477130
0.7742	Intermediate Similarity	NPC80365
0.7742	Intermediate Similarity	NPC38830
0.7738	Intermediate Similarity	NPC149550
0.7738	Intermediate Similarity	NPC203403
0.7738	Intermediate Similarity	NPC470428
0.7738	Intermediate Similarity	NPC85105
0.7732	Intermediate Similarity	NPC11956
0.7732	Intermediate Similarity	NPC32577
0.7732	Intermediate Similarity	NPC114540
0.7732	Intermediate Similarity	NPC155332
0.7727	Intermediate Similarity	NPC238485
0.7727	Intermediate Similarity	NPC102048
0.7727	Intermediate Similarity	NPC231310
0.7717	Intermediate Similarity	NPC477574
0.7717	Intermediate Similarity	NPC301244
0.7717	Intermediate Similarity	NPC473675
0.7717	Intermediate Similarity	NPC329842
0.7711	Intermediate Similarity	NPC313179
0.7711	Intermediate Similarity	NPC171148
0.7711	Intermediate Similarity	NPC69383
0.7708	Intermediate Similarity	NPC474012
0.7708	Intermediate Similarity	NPC476299
0.7701	Intermediate Similarity	NPC73882
0.7701	Intermediate Similarity	NPC202389
0.7701	Intermediate Similarity	NPC471218
0.77	Intermediate Similarity	NPC224660
0.7692	Intermediate Similarity	NPC257485
0.7692	Intermediate Similarity	NPC310236
0.7692	Intermediate Similarity	NPC470734
0.7684	Intermediate Similarity	NPC253826
0.7684	Intermediate Similarity	NPC208094
0.7684	Intermediate Similarity	NPC474785
0.7684	Intermediate Similarity	NPC108078
0.7684	Intermediate Similarity	NPC320306
0.7684	Intermediate Similarity	NPC474938
0.7674	Intermediate Similarity	NPC269791
0.7674	Intermediate Similarity	NPC472301
0.7674	Intermediate Similarity	NPC96362
0.7667	Intermediate Similarity	NPC475772
0.7667	Intermediate Similarity	NPC166857
0.7667	Intermediate Similarity	NPC473097
0.766	Intermediate Similarity	NPC53565
0.766	Intermediate Similarity	NPC472441
0.766	Intermediate Similarity	NPC88310
0.766	Intermediate Similarity	NPC276110
0.7654	Intermediate Similarity	NPC34834
0.7654	Intermediate Similarity	NPC92801
0.7653	Intermediate Similarity	NPC23584
0.7653	Intermediate Similarity	NPC72151
0.7653	Intermediate Similarity	NPC171014
0.7653	Intermediate Similarity	NPC95899
0.7647	Intermediate Similarity	NPC83351
0.7647	Intermediate Similarity	NPC17791
0.7647	Intermediate Similarity	NPC476949
0.7647	Intermediate Similarity	NPC167891
0.764	Intermediate Similarity	NPC476602
0.764	Intermediate Similarity	NPC471795
0.7634	Intermediate Similarity	NPC139692
0.7634	Intermediate Similarity	NPC134826
0.7629	Intermediate Similarity	NPC118174
0.7629	Intermediate Similarity	NPC81530
0.7629	Intermediate Similarity	NPC224720
0.7629	Intermediate Similarity	NPC476240
0.7629	Intermediate Similarity	NPC476223
0.7625	Intermediate Similarity	NPC96484
0.7619	Intermediate Similarity	NPC106432
0.7619	Intermediate Similarity	NPC253190
0.7614	Intermediate Similarity	NPC82538
0.7614	Intermediate Similarity	NPC311070
0.7614	Intermediate Similarity	NPC312480
0.7614	Intermediate Similarity	NPC237795
0.7614	Intermediate Similarity	NPC470384

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 NPC302360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1155
0.2-0.3	3586
0.3-0.4	2667
0.4-0.5	1123
0.5-0.6	287
0.6-0.7	177
0.7-0.8	10
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
0.7711	Intermediate Similarity	NPD8264	Approved
0.7604	Intermediate Similarity	NPD4225	Approved
0.7527	Intermediate Similarity	NPD7515	Phase 2
0.7447	Intermediate Similarity	NPD5779	Approved
0.7447	Intermediate Similarity	NPD5778	Approved
0.7347	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD6648	Approved
0.7273	Intermediate Similarity	NPD5344	Discontinued
0.7245	Intermediate Similarity	NPD7638	Approved
0.7188	Intermediate Similarity	NPD7748	Approved
0.7174	Intermediate Similarity	NPD3618	Phase 1
0.7158	Intermediate Similarity	NPD6079	Approved
0.7128	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6101	Approved
0.7065	Intermediate Similarity	NPD1696	Phase 3
0.7041	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5222	Approved
0.7041	Intermediate Similarity	NPD5221	Approved
0.703	Intermediate Similarity	NPD5211	Phase 2
0.7011	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7637	Suspended
0.6979	Remote Similarity	NPD6411	Approved
0.6972	Remote Similarity	NPD7115	Discovery
0.697	Remote Similarity	NPD7902	Approved
0.697	Remote Similarity	NPD5173	Approved
0.6966	Remote Similarity	NPD7645	Phase 2
0.6947	Remote Similarity	NPD5328	Approved
0.6923	Remote Similarity	NPD3667	Approved
0.6923	Remote Similarity	NPD5697	Approved
0.6897	Remote Similarity	NPD7339	Approved
0.6897	Remote Similarity	NPD6942	Approved
0.6893	Remote Similarity	NPD5141	Approved
0.6889	Remote Similarity	NPD7525	Registered
0.6889	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1694	Approved
0.6882	Remote Similarity	NPD5363	Approved
0.6875	Remote Similarity	NPD368	Approved
0.6875	Remote Similarity	NPD7838	Discovery
0.6875	Remote Similarity	NPD4192	Approved
0.6875	Remote Similarity	NPD4191	Approved
0.6875	Remote Similarity	NPD4194	Approved
0.6875	Remote Similarity	NPD4193	Approved
0.6857	Remote Similarity	NPD6011	Approved
0.6857	Remote Similarity	NPD6881	Approved
0.6857	Remote Similarity	NPD6899	Approved
0.6854	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4696	Approved
0.6832	Remote Similarity	NPD5286	Approved
0.6832	Remote Similarity	NPD5285	Approved
0.6809	Remote Similarity	NPD5279	Phase 3
0.6804	Remote Similarity	NPD5284	Approved
0.6804	Remote Similarity	NPD5281	Approved
0.6792	Remote Similarity	NPD6013	Approved
0.6792	Remote Similarity	NPD6014	Approved
0.6792	Remote Similarity	NPD6012	Approved
0.6782	Remote Similarity	NPD6926	Approved
0.6782	Remote Similarity	NPD6924	Approved
0.6778	Remote Similarity	NPD4195	Approved
0.6778	Remote Similarity	NPD6929	Approved
0.6774	Remote Similarity	NPD3665	Phase 1
0.6774	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3666	Approved
0.6774	Remote Similarity	NPD3133	Approved
0.6774	Remote Similarity	NPD4786	Approved
0.6771	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5223	Approved
0.6744	Remote Similarity	NPD7152	Approved
0.6744	Remote Similarity	NPD7151	Approved
0.6744	Remote Similarity	NPD7150	Approved
0.6739	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3573	Approved
0.6735	Remote Similarity	NPD6399	Phase 3
0.6735	Remote Similarity	NPD4202	Approved
0.6733	Remote Similarity	NPD5290	Discontinued
0.6733	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7102	Approved
0.6729	Remote Similarity	NPD7290	Approved
0.6729	Remote Similarity	NPD6883	Approved
0.6703	Remote Similarity	NPD4821	Approved
0.6703	Remote Similarity	NPD4819	Approved
0.6703	Remote Similarity	NPD7514	Phase 3
0.6703	Remote Similarity	NPD6930	Phase 2
0.6703	Remote Similarity	NPD4820	Approved
0.6703	Remote Similarity	NPD7332	Phase 2
0.6703	Remote Similarity	NPD6931	Approved
0.6703	Remote Similarity	NPD4695	Discontinued
0.6703	Remote Similarity	NPD4822	Approved
0.67	Remote Similarity	NPD4697	Phase 3
0.6699	Remote Similarity	NPD5225	Approved
0.6699	Remote Similarity	NPD5224	Approved
0.6699	Remote Similarity	NPD7632	Discontinued
0.6699	Remote Similarity	NPD5226	Approved
0.6699	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6617	Approved
0.6635	Remote Similarity	NPD5174	Approved
0.6635	Remote Similarity	NPD5175	Approved
0.6634	Remote Similarity	NPD4755	Approved
0.6632	Remote Similarity	NPD4623	Approved
0.6632	Remote Similarity	NPD4519	Discontinued
0.663	Remote Similarity	NPD4790	Discontinued
0.663	Remote Similarity	NPD6902	Approved
0.6629	Remote Similarity	NPD6933	Approved
0.6628	Remote Similarity	NPD7144	Approved
0.6628	Remote Similarity	NPD7143	Approved
0.6606	Remote Similarity	NPD6882	Approved
0.6606	Remote Similarity	NPD8297	Approved
0.6604	Remote Similarity	NPD5701	Approved
0.6596	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7503	Approved
0.6559	Remote Similarity	NPD4270	Approved
0.6559	Remote Similarity	NPD4269	Approved
0.6556	Remote Similarity	NPD6925	Approved
0.6556	Remote Similarity	NPD5776	Phase 2
0.6556	Remote Similarity	NPD4756	Discovery
0.6545	Remote Similarity	NPD4632	Approved
0.6542	Remote Similarity	NPD7320	Approved
0.6538	Remote Similarity	NPD342	Phase 1
0.6531	Remote Similarity	NPD5785	Approved
0.6526	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7509	Discontinued
0.6512	Remote Similarity	NPD6922	Approved
0.6512	Remote Similarity	NPD6923	Approved
0.6505	Remote Similarity	NPD4700	Approved
0.6505	Remote Similarity	NPD6404	Discontinued
0.6489	Remote Similarity	NPD7154	Phase 3
0.6484	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6373	Approved
0.6481	Remote Similarity	NPD6372	Approved
0.6471	Remote Similarity	NPD6084	Phase 2
0.6471	Remote Similarity	NPD6083	Phase 2
0.6458	Remote Similarity	NPD7521	Approved
0.6458	Remote Similarity	NPD5330	Approved
0.6458	Remote Similarity	NPD6684	Approved
0.6458	Remote Similarity	NPD7146	Approved
0.6458	Remote Similarity	NPD7334	Approved
0.6458	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6409	Approved
0.6436	Remote Similarity	NPD5210	Approved
0.6436	Remote Similarity	NPD4629	Approved
0.6436	Remote Similarity	NPD5695	Phase 3
0.6429	Remote Similarity	NPD4753	Phase 2
0.6429	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD6051	Approved
0.6421	Remote Similarity	NPD3668	Phase 3
0.6392	Remote Similarity	NPD7750	Discontinued
0.6392	Remote Similarity	NPD7524	Approved
0.6389	Remote Similarity	NPD5168	Approved
0.6389	Remote Similarity	NPD4729	Approved
0.6389	Remote Similarity	NPD4730	Approved
0.6374	Remote Similarity	NPD6932	Approved
0.6372	Remote Similarity	NPD6009	Approved
0.6372	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6893	Approved
0.6344	Remote Similarity	NPD4748	Discontinued
0.6344	Remote Similarity	NPD4252	Approved
0.6341	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6672	Approved
0.6327	Remote Similarity	NPD5737	Approved
0.6327	Remote Similarity	NPD6903	Approved
0.6321	Remote Similarity	NPD4754	Approved
0.6321	Remote Similarity	NPD6647	Phase 2
0.6316	Remote Similarity	NPD6335	Approved
0.6316	Remote Similarity	NPD6313	Approved
0.6316	Remote Similarity	NPD6314	Approved
0.63	Remote Similarity	NPD5694	Approved
0.63	Remote Similarity	NPD7983	Approved
0.6289	Remote Similarity	NPD5280	Approved
0.6289	Remote Similarity	NPD5690	Phase 2
0.6289	Remote Similarity	NPD5786	Approved
0.6289	Remote Similarity	NPD4694	Approved
0.6283	Remote Similarity	NPD6274	Approved
0.6277	Remote Similarity	NPD6898	Phase 1
0.6273	Remote Similarity	NPD5250	Approved
0.6273	Remote Similarity	NPD4634	Approved
0.6273	Remote Similarity	NPD5249	Phase 3
0.6273	Remote Similarity	NPD5169	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