NPASS Compound

Structure

CID99380 OpenBabel06191715442D 24 26 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 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 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 -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 2.5981 -0.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 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 1.0000 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 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 2.5981 1.5000 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 1 11 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 10 21 2 0 0 0 0 12 11 1 6 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 22 1 1 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	1.803
LogD:	1.413
LogS:	-3.403
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.727
Synthetic Accessibility Score:	4.547
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.85
MDCK Permeability:	1.7286560250795446e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.756
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.776
Plasma Protein Binding (PPB):	56.031227111816406%
Volume Distribution (VD):	1.646
Pgp-substrate:	45.863136291503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.479
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.352
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.51

ADMET: Excretion

Clearance (CL):	4.303
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.057
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.614
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.229

Download Data

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

Natural Product: NPC99380

Natural Product ID:	NPC99380
*Common Name:**	Eriocasin B
IUPAC Name:	2-[(2R,4bR,7R,8aS,9S)-7,9-dihydroxy-4b,8,8-trimethyl-10-oxo-2,3,4,5,6,7,8a,9-octahydro-1H-phenanthren-2-yl]prop-2-enal
Synonyms:	Eriocasin B
Standard InCHIKey:	KHXPUTCGVCTBNK-IBKORDLPSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-11(10-21)12-5-6-14-13(9-12)16(23)17(24)18-19(2,3)15(22)7-8-20(14,18)4/h10,12,15,17-18,22,24H,1,5-9H2,2-4H3/t12-,15-,17-,18-,20+/m1/s1
SMILES:	O=CC(=C)[C@@H]1CCC2=C(C1)C(=O)[C@H]([C@H]1[C@@]2(C)CC[C@H](C1(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641887
PubChem CID:	50901031
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[481213]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[481213]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[481213]

☑ 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 NPC99380 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	198
0.1-0.2	1388
0.2-0.3	5170
0.3-0.4	11150
0.4-0.5	12176
0.5-0.6	6974
0.6-0.7	4319
0.7-0.8	1220
0.8-0.85	92
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC34190
0.8778	High Similarity	NPC183283
0.871	High Similarity	NPC96859
0.871	High Similarity	NPC305483
0.871	High Similarity	NPC192428
0.871	High Similarity	NPC328162
0.8696	High Similarity	NPC23170
0.8681	High Similarity	NPC185936
0.8681	High Similarity	NPC168027
0.8667	High Similarity	NPC472983
0.8571	High Similarity	NPC191684
0.8556	High Similarity	NPC473229
0.8556	High Similarity	NPC206060
0.8556	High Similarity	NPC143767
0.8556	High Similarity	NPC131470
0.8556	High Similarity	NPC474925
0.8523	High Similarity	NPC470812
0.8511	High Similarity	NPC5532
0.8511	High Similarity	NPC469545
0.8511	High Similarity	NPC61369
0.8506	High Similarity	NPC103486
0.8495	Intermediate Similarity	NPC166906
0.8462	Intermediate Similarity	NPC275740
0.8462	Intermediate Similarity	NPC86319
0.8438	Intermediate Similarity	NPC144956
0.8427	Intermediate Similarity	NPC32037
0.8421	Intermediate Similarity	NPC18509
0.8421	Intermediate Similarity	NPC43747
0.8409	Intermediate Similarity	NPC64600
0.8404	Intermediate Similarity	NPC470016
0.8404	Intermediate Similarity	NPC317586
0.8404	Intermediate Similarity	NPC474602
0.8391	Intermediate Similarity	NPC119229
0.8391	Intermediate Similarity	NPC55869
0.8387	Intermediate Similarity	NPC477436
0.8387	Intermediate Similarity	NPC477435
0.8352	Intermediate Similarity	NPC471722
0.8352	Intermediate Similarity	NPC328539
0.8352	Intermediate Similarity	NPC230387
0.8352	Intermediate Similarity	NPC158778
0.8351	Intermediate Similarity	NPC472637
0.8351	Intermediate Similarity	NPC163372
0.8351	Intermediate Similarity	NPC302537
0.8333	Intermediate Similarity	NPC472974
0.8333	Intermediate Similarity	NPC94666
0.8333	Intermediate Similarity	NPC72133
0.8298	Intermediate Similarity	NPC272635
0.8298	Intermediate Similarity	NPC472977
0.8298	Intermediate Similarity	NPC169751
0.8298	Intermediate Similarity	NPC196485
0.8298	Intermediate Similarity	NPC245972
0.8298	Intermediate Similarity	NPC472976
0.8298	Intermediate Similarity	NPC474328
0.8295	Intermediate Similarity	NPC48362
0.828	Intermediate Similarity	NPC172101
0.828	Intermediate Similarity	NPC472978
0.828	Intermediate Similarity	NPC63748
0.8276	Intermediate Similarity	NPC108955
0.8265	Intermediate Similarity	NPC119601
0.8265	Intermediate Similarity	NPC308726
0.8261	Intermediate Similarity	NPC119416
0.8261	Intermediate Similarity	NPC472973
0.8247	Intermediate Similarity	NPC472972
0.8242	Intermediate Similarity	NPC272039
0.8242	Intermediate Similarity	NPC472324
0.8242	Intermediate Similarity	NPC220930
0.8222	Intermediate Similarity	NPC8518
0.8222	Intermediate Similarity	NPC263997
0.8222	Intermediate Similarity	NPC197823
0.8222	Intermediate Similarity	NPC132228
0.8211	Intermediate Similarity	NPC473170
0.8211	Intermediate Similarity	NPC139570
0.8211	Intermediate Similarity	NPC477437
0.8211	Intermediate Similarity	NPC477438
0.8191	Intermediate Similarity	NPC134826
0.8191	Intermediate Similarity	NPC69454
0.8191	Intermediate Similarity	NPC211230
0.8182	Intermediate Similarity	NPC116797
0.8172	Intermediate Similarity	NPC134321
0.8172	Intermediate Similarity	NPC128672
0.8163	Intermediate Similarity	NPC470184
0.8161	Intermediate Similarity	NPC470429
0.8152	Intermediate Similarity	NPC471724
0.8144	Intermediate Similarity	NPC114274
0.814	Intermediate Similarity	NPC197659
0.8132	Intermediate Similarity	NPC20688
0.8132	Intermediate Similarity	NPC327115
0.8132	Intermediate Similarity	NPC158393
0.8132	Intermediate Similarity	NPC94755
0.8125	Intermediate Similarity	NPC249954
0.8125	Intermediate Similarity	NPC117133
0.8125	Intermediate Similarity	NPC165616
0.8125	Intermediate Similarity	NPC473158
0.8125	Intermediate Similarity	NPC219353
0.8119	Intermediate Similarity	NPC472925
0.8105	Intermediate Similarity	NPC196227
0.8105	Intermediate Similarity	NPC160413
0.8105	Intermediate Similarity	NPC477439
0.8105	Intermediate Similarity	NPC103527
0.8105	Intermediate Similarity	NPC471207
0.8105	Intermediate Similarity	NPC212812
0.809	Intermediate Similarity	NPC470813
0.8085	Intermediate Similarity	NPC155304
0.8085	Intermediate Similarity	NPC248913
0.8085	Intermediate Similarity	NPC472975
0.8085	Intermediate Similarity	NPC73457
0.8081	Intermediate Similarity	NPC473424
0.8068	Intermediate Similarity	NPC2482
0.8065	Intermediate Similarity	NPC31985
0.8065	Intermediate Similarity	NPC474245
0.8065	Intermediate Similarity	NPC1015
0.8065	Intermediate Similarity	NPC184663
0.8061	Intermediate Similarity	NPC15390
0.8061	Intermediate Similarity	NPC316964
0.8061	Intermediate Similarity	NPC157787
0.8061	Intermediate Similarity	NPC327431
0.8061	Intermediate Similarity	NPC88198
0.8046	Intermediate Similarity	NPC253561
0.8046	Intermediate Similarity	NPC80088
0.8046	Intermediate Similarity	NPC178852
0.8046	Intermediate Similarity	NPC30321
0.8043	Intermediate Similarity	NPC298904
0.8043	Intermediate Similarity	NPC174619
0.8043	Intermediate Similarity	NPC475740
0.8041	Intermediate Similarity	NPC273269
0.8039	Intermediate Similarity	NPC295244
0.8023	Intermediate Similarity	NPC92080
0.8023	Intermediate Similarity	NPC470525
0.8022	Intermediate Similarity	NPC470574
0.8022	Intermediate Similarity	NPC79573
0.8022	Intermediate Similarity	NPC6185
0.8022	Intermediate Similarity	NPC36350
0.8022	Intermediate Similarity	NPC241512
0.8022	Intermediate Similarity	NPC476426
0.8021	Intermediate Similarity	NPC259286
0.8021	Intermediate Similarity	NPC173875
0.8021	Intermediate Similarity	NPC200702
0.8021	Intermediate Similarity	NPC142352
0.8021	Intermediate Similarity	NPC318282
0.8021	Intermediate Similarity	NPC174948
0.8021	Intermediate Similarity	NPC29112
0.8021	Intermediate Similarity	NPC280725
0.8021	Intermediate Similarity	NPC469995
0.8	Intermediate Similarity	NPC159442
0.8	Intermediate Similarity	NPC275583
0.8	Intermediate Similarity	NPC12722
0.8	Intermediate Similarity	NPC59350
0.8	Intermediate Similarity	NPC472930
0.8	Intermediate Similarity	NPC475255
0.8	Intermediate Similarity	NPC250575
0.8	Intermediate Similarity	NPC95585
0.8	Intermediate Similarity	NPC282233
0.798	Intermediate Similarity	NPC81530
0.798	Intermediate Similarity	NPC60947
0.7979	Intermediate Similarity	NPC475823
0.7979	Intermediate Similarity	NPC474209
0.7979	Intermediate Similarity	NPC129913
0.7979	Intermediate Similarity	NPC472325
0.7979	Intermediate Similarity	NPC85173
0.7978	Intermediate Similarity	NPC328264
0.7978	Intermediate Similarity	NPC121984
0.7978	Intermediate Similarity	NPC473420
0.7959	Intermediate Similarity	NPC478056
0.7959	Intermediate Similarity	NPC147954
0.7959	Intermediate Similarity	NPC194196
0.7957	Intermediate Similarity	NPC185059
0.7957	Intermediate Similarity	NPC470524
0.7957	Intermediate Similarity	NPC474677
0.7957	Intermediate Similarity	NPC472802
0.7957	Intermediate Similarity	NPC242864
0.7957	Intermediate Similarity	NPC475001
0.7957	Intermediate Similarity	NPC307298
0.7955	Intermediate Similarity	NPC472490
0.7955	Intermediate Similarity	NPC281138
0.7941	Intermediate Similarity	NPC144854
0.7941	Intermediate Similarity	NPC44063
0.7941	Intermediate Similarity	NPC3316
0.7938	Intermediate Similarity	NPC157113
0.7938	Intermediate Similarity	NPC62516
0.7938	Intermediate Similarity	NPC95565
0.7938	Intermediate Similarity	NPC471039
0.7938	Intermediate Similarity	NPC328371
0.7935	Intermediate Similarity	NPC235341
0.7935	Intermediate Similarity	NPC95594
0.7935	Intermediate Similarity	NPC474733
0.7935	Intermediate Similarity	NPC118648
0.7935	Intermediate Similarity	NPC222613
0.7935	Intermediate Similarity	NPC472985
0.7935	Intermediate Similarity	NPC51014
0.7935	Intermediate Similarity	NPC31564
0.7935	Intermediate Similarity	NPC475022
0.7935	Intermediate Similarity	NPC474778
0.7935	Intermediate Similarity	NPC145879
0.7935	Intermediate Similarity	NPC473226
0.7935	Intermediate Similarity	NPC477579
0.7935	Intermediate Similarity	NPC474732
0.7935	Intermediate Similarity	NPC472986
0.7931	Intermediate Similarity	NPC470428
0.7921	Intermediate Similarity	NPC96268
0.7921	Intermediate Similarity	NPC213366

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 NPC99380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1872
0.2-0.3	3889
0.3-0.4	2199
0.4-0.5	613
0.5-0.6	176
0.6-0.7	128
0.7-0.8	89
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD4697	Phase 3
0.8511	High Similarity	NPD5221	Approved
0.8511	High Similarity	NPD5220	Clinical (unspecified phase)
0.8511	High Similarity	NPD5222	Approved
0.8438	Intermediate Similarity	NPD5285	Approved
0.8438	Intermediate Similarity	NPD4696	Approved
0.8438	Intermediate Similarity	NPD5286	Approved
0.8421	Intermediate Similarity	NPD4755	Approved
0.8421	Intermediate Similarity	NPD5173	Approved
0.8351	Intermediate Similarity	NPD5223	Approved
0.828	Intermediate Similarity	NPD6079	Approved
0.8265	Intermediate Similarity	NPD5211	Phase 2
0.8265	Intermediate Similarity	NPD5226	Approved
0.8265	Intermediate Similarity	NPD5225	Approved
0.8265	Intermediate Similarity	NPD5224	Approved
0.8265	Intermediate Similarity	NPD4633	Approved
0.8261	Intermediate Similarity	NPD5328	Approved
0.8247	Intermediate Similarity	NPD4700	Approved
0.8182	Intermediate Similarity	NPD5174	Approved
0.8182	Intermediate Similarity	NPD5175	Approved
0.8132	Intermediate Similarity	NPD3618	Phase 1
0.81	Intermediate Similarity	NPD5141	Approved
0.8068	Intermediate Similarity	NPD4695	Discontinued
0.8	Intermediate Similarity	NPD4754	Approved
0.7941	Intermediate Similarity	NPD5697	Approved
0.7935	Intermediate Similarity	NPD5279	Phase 3
0.7895	Intermediate Similarity	NPD7515	Phase 2
0.7889	Intermediate Similarity	NPD3667	Approved
0.7864	Intermediate Similarity	NPD4730	Approved
0.7864	Intermediate Similarity	NPD4729	Approved
0.7864	Intermediate Similarity	NPD6011	Approved
0.7864	Intermediate Similarity	NPD5128	Approved
0.7864	Intermediate Similarity	NPD6881	Approved
0.7864	Intermediate Similarity	NPD6899	Approved
0.7843	Intermediate Similarity	NPD6675	Approved
0.7843	Intermediate Similarity	NPD5739	Approved
0.7843	Intermediate Similarity	NPD4768	Approved
0.7843	Intermediate Similarity	NPD4767	Approved
0.7843	Intermediate Similarity	NPD6402	Approved
0.7843	Intermediate Similarity	NPD7128	Approved
0.7812	Intermediate Similarity	NPD4202	Approved
0.7788	Intermediate Similarity	NPD6014	Approved
0.7788	Intermediate Similarity	NPD6013	Approved
0.7788	Intermediate Similarity	NPD6012	Approved
0.7767	Intermediate Similarity	NPD5701	Approved
0.7717	Intermediate Similarity	NPD4786	Approved
0.7717	Intermediate Similarity	NPD3133	Approved
0.7717	Intermediate Similarity	NPD3666	Approved
0.7717	Intermediate Similarity	NPD3665	Phase 1
0.7714	Intermediate Similarity	NPD6883	Approved
0.7714	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4634	Approved
0.7714	Intermediate Similarity	NPD7102	Approved
0.7714	Intermediate Similarity	NPD5135	Approved
0.7714	Intermediate Similarity	NPD7290	Approved
0.7714	Intermediate Similarity	NPD5249	Phase 3
0.7714	Intermediate Similarity	NPD5169	Approved
0.7714	Intermediate Similarity	NPD5248	Approved
0.7714	Intermediate Similarity	NPD5251	Approved
0.7714	Intermediate Similarity	NPD5247	Approved
0.7714	Intermediate Similarity	NPD5250	Approved
0.7692	Intermediate Similarity	NPD7320	Approved
0.7692	Intermediate Similarity	NPD5168	Approved
0.7684	Intermediate Similarity	NPD4753	Phase 2
0.7642	Intermediate Similarity	NPD8130	Phase 1
0.7642	Intermediate Similarity	NPD5216	Approved
0.7642	Intermediate Similarity	NPD6650	Approved
0.7642	Intermediate Similarity	NPD6869	Approved
0.7642	Intermediate Similarity	NPD5127	Approved
0.7642	Intermediate Similarity	NPD6847	Approved
0.7642	Intermediate Similarity	NPD5217	Approved
0.7642	Intermediate Similarity	NPD5215	Approved
0.7642	Intermediate Similarity	NPD6649	Approved
0.7642	Intermediate Similarity	NPD6617	Approved
0.7619	Intermediate Similarity	NPD6372	Approved
0.7619	Intermediate Similarity	NPD6373	Approved
0.757	Intermediate Similarity	NPD8297	Approved
0.757	Intermediate Similarity	NPD6882	Approved
0.7553	Intermediate Similarity	NPD5690	Phase 2
0.7551	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.7477	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4629	Approved
0.7475	Intermediate Similarity	NPD5210	Approved
0.7473	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3617	Approved
0.7431	Intermediate Similarity	NPD5167	Approved
0.7368	Intermediate Similarity	NPD5280	Approved
0.7368	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4694	Approved
0.7364	Intermediate Similarity	NPD6274	Approved
0.734	Intermediate Similarity	NPD3668	Phase 3
0.734	Intermediate Similarity	NPD4197	Approved
0.732	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5695	Phase 3
0.7297	Intermediate Similarity	NPD6009	Approved
0.7297	Intermediate Similarity	NPD6317	Approved
0.7292	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.7263	Intermediate Similarity	NPD5329	Approved
0.7232	Intermediate Similarity	NPD6313	Approved
0.7232	Intermediate Similarity	NPD6314	Approved
0.7232	Intermediate Similarity	NPD6335	Approved
0.7207	Intermediate Similarity	NPD6868	Approved
0.72	Intermediate Similarity	NPD7900	Approved
0.72	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6411	Approved
0.7168	Intermediate Similarity	NPD7100	Approved
0.7168	Intermediate Similarity	NPD7101	Approved
0.7157	Intermediate Similarity	NPD6084	Phase 2
0.7157	Intermediate Similarity	NPD6083	Phase 2
0.7128	Intermediate Similarity	NPD4221	Approved
0.7128	Intermediate Similarity	NPD4223	Phase 3
0.7105	Intermediate Similarity	NPD6054	Approved
0.7105	Intermediate Similarity	NPD6319	Approved
0.7083	Intermediate Similarity	NPD1696	Phase 3
0.7043	Intermediate Similarity	NPD6015	Approved
0.7043	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6016	Approved
0.7043	Intermediate Similarity	NPD5983	Phase 2
0.7041	Intermediate Similarity	NPD6672	Approved
0.7041	Intermediate Similarity	NPD5737	Approved
0.7009	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD5284	Approved
0.7	Intermediate Similarity	NPD5281	Approved
0.6983	Remote Similarity	NPD6370	Approved
0.6983	Remote Similarity	NPD5988	Approved
0.697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6101	Approved
0.6957	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD7604	Phase 2
0.6915	Remote Similarity	NPD7525	Registered
0.6907	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6909	Approved
0.6897	Remote Similarity	NPD6908	Approved
0.6875	Remote Similarity	NPD4788	Approved
0.6864	Remote Similarity	NPD7492	Approved
0.6848	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4689	Approved
0.6837	Remote Similarity	NPD4693	Phase 3
0.6837	Remote Similarity	NPD4688	Approved
0.6837	Remote Similarity	NPD7521	Approved
0.6837	Remote Similarity	NPD4138	Approved
0.6837	Remote Similarity	NPD6684	Approved
0.6837	Remote Similarity	NPD4690	Approved
0.6837	Remote Similarity	NPD6409	Approved
0.6837	Remote Similarity	NPD4519	Discontinued
0.6837	Remote Similarity	NPD7334	Approved
0.6837	Remote Similarity	NPD5205	Approved
0.6837	Remote Similarity	NPD4623	Approved
0.6837	Remote Similarity	NPD5330	Approved
0.6837	Remote Similarity	NPD7146	Approved
0.6809	Remote Similarity	NPD7645	Phase 2
0.6807	Remote Similarity	NPD6616	Approved
0.6807	Remote Similarity	NPD6336	Discontinued
0.678	Remote Similarity	NPD8328	Phase 3
0.6765	Remote Similarity	NPD5133	Approved
0.6762	Remote Similarity	NPD7638	Approved
0.675	Remote Similarity	NPD7078	Approved
0.6739	Remote Similarity	NPD6942	Approved
0.6739	Remote Similarity	NPD3703	Phase 2
0.6739	Remote Similarity	NPD7339	Approved
0.6733	Remote Similarity	NPD5692	Phase 3
0.6731	Remote Similarity	NPD7614	Phase 1
0.67	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6903	Approved
0.6698	Remote Similarity	NPD7640	Approved
0.6698	Remote Similarity	NPD7639	Approved
0.6696	Remote Similarity	NPD7115	Discovery
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD4691	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6634	Remote Similarity	NPD6673	Approved
0.6634	Remote Similarity	NPD6080	Approved
0.6634	Remote Similarity	NPD6904	Approved
0.6632	Remote Similarity	NPD4195	Approved
0.6612	Remote Similarity	NPD8293	Discontinued
0.6604	Remote Similarity	NPD4225	Approved
0.6604	Remote Similarity	NPD5290	Discontinued
0.6602	Remote Similarity	NPD5778	Approved
0.6602	Remote Similarity	NPD5779	Approved
0.6591	Remote Similarity	NPD7331	Phase 2
0.6574	Remote Similarity	NPD5091	Approved
0.6569	Remote Similarity	NPD4096	Approved
0.6566	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD4748	Discontinued
0.6557	Remote Similarity	NPD6033	Approved
0.6556	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4137	Phase 3
0.6552	Remote Similarity	NPD8295	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