NPASS Compound

Structure

NPC310752 OpenBabel07101719512D 33 35 0 0 1 0 0 0 0 0999 V2000 -5.7396 6.6391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3869 6.1039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 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 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1216 4.7370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0997 4.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8126 3.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 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 -3.0000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4087 5.8959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8344 3.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -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 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 2 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 0.8660 -1.5000 0.0000 C 0 0 2 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 4.0981 -0.6340 0.0000 O 0 0 0 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 8 10 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 9 13 2 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 21 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 0 0 0 0 16 29 1 0 0 0 0 17 28 1 0 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 19 30 1 0 0 0 0 19 31 1 0 0 0 0 22 27 2 0 0 0 0 23 27 1 0 0 0 0 23 32 2 0 0 0 0 24 28 1 1 0 0 0 24 30 1 0 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 26 30 1 6 0 0 0 26 33 1 0 0 0 0 27 29 1 0 0 0 0 28 5 1 1 0 0 0 29 6 1 6 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.33
Volume:	512.319
LogP:	4.327
LogD:	3.915
LogS:	-4.865
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	4.831
Fsp3:	0.633
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.951
MDCK Permeability:	2.403592225164175e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.844
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	96.93427276611328%
Volume Distribution (VD):	1.456
Pgp-substrate:	4.643383979797363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.292
CYP1A2-substrate:	0.532
CYP2C19-inhibitor:	0.362
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.339
CYP2C9-substrate:	0.832
CYP2D6-inhibitor:	0.919
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.703

ADMET: Excretion

Clearance (CL):	5.394
Half-life (T1/2):	0.333

ADMET: Toxicity

hERG Blockers:	0.461
Human Hepatotoxicity (H-HT):	0.356
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.952
Carcinogencity:	0.176
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC310752

Natural Product ID:	NPC310752
*Common Name:**	Stellettin J
IUPAC Name:	(3Z,3aS,5aR,6S,7R,9aR,9bS)-3-[(3E,5E,7E)-6,10-dimethylundeca-3,5,7,9-tetraen-2-ylidene]-7-hydroxy-6-(hydroxymethyl)-3a,6,9a-trimethyl-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-2-one
Synonyms:	Stellettin J
Standard InCHIKey:	MDQDLERKDZJSCM-BYBVMEJRSA-N
Standard InCHI:	InChI=1S/C30H44O3/c1-20(2)10-8-11-21(3)12-9-13-22(4)27-23(32)18-25-28(5)17-15-26(33)30(7,19-31)24(28)14-16-29(25,27)6/h8-13,24-26,31,33H,14-19H2,1-7H3/b11-8+,13-9+,21-12+,27-22+/t24-,25+,26-,28+,29+,30-/m1/s1
SMILES:	CC(=C/C=C/C(=C/C=C/C(=C/1C(=O)C[C@H]2[C@@]3(C)CC[C@H]([C@](C)(CO)[C@@H]3CC[C@]12C)O)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481244
PubChem CID:	11683868
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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	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
Others	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	1.2	uM	PMID[452426]
NPT2	Others	Unspecified		Activity	=	8.0	%	PMID[452426]

☑ 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 NPC310752 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	4013
0.3-0.4	11424
0.4-0.5	11651
0.5-0.6	6785
0.6-0.7	5231
0.7-0.8	2272
0.8-0.85	173
0.85-0.9	74
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC292491
0.9878	High Similarity	NPC141292
0.9425	High Similarity	NPC474690
0.9318	High Similarity	NPC88310
0.9318	High Similarity	NPC180950
0.9213	High Similarity	NPC471153
0.9205	High Similarity	NPC299100
0.9167	High Similarity	NPC470574
0.9111	High Similarity	NPC474785
0.9111	High Similarity	NPC474938
0.9	High Similarity	NPC250757
0.9	High Similarity	NPC301534
0.8989	High Similarity	NPC209662
0.8977	High Similarity	NPC272746
0.8966	High Similarity	NPC1015
0.8966	High Similarity	NPC31985
0.8953	High Similarity	NPC58063
0.8953	High Similarity	NPC475740
0.8864	High Similarity	NPC126993
0.8851	High Similarity	NPC471722
0.8851	High Similarity	NPC328539
0.8837	High Similarity	NPC474733
0.8837	High Similarity	NPC474778
0.8837	High Similarity	NPC145879
0.8837	High Similarity	NPC474732
0.8837	High Similarity	NPC31564
0.8837	High Similarity	NPC72133
0.8824	High Similarity	NPC85774
0.8824	High Similarity	NPC214043
0.8817	High Similarity	NPC115899
0.8817	High Similarity	NPC282524
0.8804	High Similarity	NPC108368
0.8804	High Similarity	NPC103051
0.8804	High Similarity	NPC57079
0.8764	High Similarity	NPC475806
0.875	High Similarity	NPC275740
0.875	High Similarity	NPC473999
0.875	High Similarity	NPC86319
0.875	High Similarity	NPC309603
0.8736	High Similarity	NPC136548
0.8723	High Similarity	NPC155332
0.8723	High Similarity	NPC114540
0.8723	High Similarity	NPC32577
0.871	High Similarity	NPC266955
0.871	High Similarity	NPC35751
0.8681	High Similarity	NPC280725
0.8667	High Similarity	NPC475255
0.8667	High Similarity	NPC12722
0.8667	High Similarity	NPC134826
0.8652	High Similarity	NPC475965
0.8652	High Similarity	NPC48010
0.8652	High Similarity	NPC474842
0.8652	High Similarity	NPC191684
0.8652	High Similarity	NPC85173
0.8636	High Similarity	NPC131470
0.8636	High Similarity	NPC143767
0.8636	High Similarity	NPC193360
0.8632	High Similarity	NPC475050
0.8621	High Similarity	NPC222613
0.8621	High Similarity	NPC475022
0.8621	High Similarity	NPC118648
0.8605	High Similarity	NPC59453
0.8605	High Similarity	NPC329043
0.8605	High Similarity	NPC58841
0.8605	High Similarity	NPC321187
0.8605	High Similarity	NPC161423
0.8605	High Similarity	NPC227064
0.8605	High Similarity	NPC473246
0.8605	High Similarity	NPC221758
0.8602	High Similarity	NPC191565
0.8588	High Similarity	NPC151519
0.8571	High Similarity	NPC471078
0.8571	High Similarity	NPC473280
0.8571	High Similarity	NPC473435
0.8571	High Similarity	NPC245972
0.8571	High Similarity	NPC473172
0.8571	High Similarity	NPC8993
0.8571	High Similarity	NPC473431
0.8571	High Similarity	NPC111015
0.8571	High Similarity	NPC196485
0.8556	High Similarity	NPC473998
0.8556	High Similarity	NPC473167
0.8556	High Similarity	NPC168027
0.8556	High Similarity	NPC185936
0.8556	High Similarity	NPC155304
0.8539	High Similarity	NPC84271
0.8539	High Similarity	NPC26959
0.8539	High Similarity	NPC128496
0.8539	High Similarity	NPC474704
0.8539	High Similarity	NPC268406
0.8539	High Similarity	NPC77168
0.8539	High Similarity	NPC186688
0.8539	High Similarity	NPC119416
0.8539	High Similarity	NPC102414
0.8539	High Similarity	NPC475921
0.8523	High Similarity	NPC142361
0.8523	High Similarity	NPC93778
0.8523	High Similarity	NPC474684
0.8506	High Similarity	NPC197823
0.8506	High Similarity	NPC469948
0.8495	Intermediate Similarity	NPC108078
0.8488	Intermediate Similarity	NPC64600
0.8478	Intermediate Similarity	NPC271195
0.8478	Intermediate Similarity	NPC259286
0.8478	Intermediate Similarity	NPC473170
0.8471	Intermediate Similarity	NPC121984
0.8462	Intermediate Similarity	NPC69454
0.8454	Intermediate Similarity	NPC266570
0.8452	Intermediate Similarity	NPC229204
0.8444	Intermediate Similarity	NPC183283
0.8438	Intermediate Similarity	NPC72151
0.8434	Intermediate Similarity	NPC197659
0.8427	Intermediate Similarity	NPC471724
0.8427	Intermediate Similarity	NPC474677
0.8427	Intermediate Similarity	NPC472802
0.8409	Intermediate Similarity	NPC51014
0.8409	Intermediate Similarity	NPC213412
0.8409	Intermediate Similarity	NPC473168
0.8409	Intermediate Similarity	NPC94755
0.8409	Intermediate Similarity	NPC158393
0.8409	Intermediate Similarity	NPC327115
0.8409	Intermediate Similarity	NPC94666
0.8409	Intermediate Similarity	NPC471737
0.8391	Intermediate Similarity	NPC82902
0.8391	Intermediate Similarity	NPC237712
0.8391	Intermediate Similarity	NPC33913
0.8391	Intermediate Similarity	NPC472265
0.8387	Intermediate Similarity	NPC106425
0.8387	Intermediate Similarity	NPC122324
0.8387	Intermediate Similarity	NPC249954
0.8387	Intermediate Similarity	NPC473164
0.8387	Intermediate Similarity	NPC151725
0.8372	Intermediate Similarity	NPC48362
0.837	Intermediate Similarity	NPC49670
0.837	Intermediate Similarity	NPC471207
0.8367	Intermediate Similarity	NPC330011
0.8367	Intermediate Similarity	NPC473284
0.8367	Intermediate Similarity	NPC329048
0.8353	Intermediate Similarity	NPC2482
0.8353	Intermediate Similarity	NPC164999
0.8352	Intermediate Similarity	NPC19114
0.8352	Intermediate Similarity	NPC233116
0.8352	Intermediate Similarity	NPC131872
0.8352	Intermediate Similarity	NPC63748
0.8333	Intermediate Similarity	NPC477943
0.8333	Intermediate Similarity	NPC77263
0.8333	Intermediate Similarity	NPC474245
0.8333	Intermediate Similarity	NPC250592
0.8333	Intermediate Similarity	NPC32830
0.8333	Intermediate Similarity	NPC320447
0.8316	Intermediate Similarity	NPC144956
0.8315	Intermediate Similarity	NPC187376
0.8315	Intermediate Similarity	NPC287079
0.8315	Intermediate Similarity	NPC475772
0.8315	Intermediate Similarity	NPC233836
0.8315	Intermediate Similarity	NPC159046
0.8315	Intermediate Similarity	NPC90652
0.8298	Intermediate Similarity	NPC18509
0.8298	Intermediate Similarity	NPC110937
0.8295	Intermediate Similarity	NPC22133
0.8295	Intermediate Similarity	NPC471224
0.8295	Intermediate Similarity	NPC474218
0.8295	Intermediate Similarity	NPC76518
0.8295	Intermediate Similarity	NPC133954
0.828	Intermediate Similarity	NPC139459
0.8276	Intermediate Similarity	NPC475726
0.8276	Intermediate Similarity	NPC476082
0.8276	Intermediate Similarity	NPC312480
0.8276	Intermediate Similarity	NPC278648
0.8276	Intermediate Similarity	NPC472743
0.8261	Intermediate Similarity	NPC250575
0.8261	Intermediate Similarity	NPC474736
0.8261	Intermediate Similarity	NPC472930
0.8261	Intermediate Similarity	NPC477520
0.8261	Intermediate Similarity	NPC109305
0.8256	Intermediate Similarity	NPC473217
0.8256	Intermediate Similarity	NPC136150
0.8247	Intermediate Similarity	NPC247957
0.8247	Intermediate Similarity	NPC249187
0.8247	Intermediate Similarity	NPC329345
0.8247	Intermediate Similarity	NPC473283
0.8247	Intermediate Similarity	NPC475526
0.8242	Intermediate Similarity	NPC129913
0.8235	Intermediate Similarity	NPC474113
0.8222	Intermediate Similarity	NPC206060
0.8222	Intermediate Similarity	NPC328313
0.8222	Intermediate Similarity	NPC470417
0.8222	Intermediate Similarity	NPC104560
0.8222	Intermediate Similarity	NPC158778
0.8222	Intermediate Similarity	NPC53911
0.8222	Intermediate Similarity	NPC44181
0.8214	Intermediate Similarity	NPC472746
0.8211	Intermediate Similarity	NPC114274
0.8202	Intermediate Similarity	NPC155011
0.8202	Intermediate Similarity	NPC475862
0.8202	Intermediate Similarity	NPC179591
0.8202	Intermediate Similarity	NPC74363
0.8202	Intermediate Similarity	NPC28252
0.8202	Intermediate Similarity	NPC472985
0.8202	Intermediate Similarity	NPC472986

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 NPC310752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1139
0.2-0.3	3722
0.3-0.4	2774
0.4-0.5	842
0.5-0.6	209
0.6-0.7	128
0.7-0.8	158
0.8-0.85	22
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9059	High Similarity	NPD3618	Phase 1
0.8977	High Similarity	NPD6079	Approved
0.8966	High Similarity	NPD5328	Approved
0.8605	High Similarity	NPD4786	Approved
0.8605	High Similarity	NPD3665	Phase 1
0.8605	High Similarity	NPD3133	Approved
0.8605	High Similarity	NPD3666	Approved
0.8588	High Similarity	NPD3667	Approved
0.8462	Intermediate Similarity	NPD4202	Approved
0.8409	Intermediate Similarity	NPD5279	Phase 3
0.8387	Intermediate Similarity	NPD5222	Approved
0.8387	Intermediate Similarity	NPD5221	Approved
0.8387	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD4696	Approved
0.8316	Intermediate Similarity	NPD5286	Approved
0.8316	Intermediate Similarity	NPD5285	Approved
0.8298	Intermediate Similarity	NPD4755	Approved
0.8298	Intermediate Similarity	NPD5173	Approved
0.8191	Intermediate Similarity	NPD4697	Phase 3
0.8152	Intermediate Similarity	NPD7515	Phase 2
0.8144	Intermediate Similarity	NPD5224	Approved
0.8144	Intermediate Similarity	NPD5226	Approved
0.8144	Intermediate Similarity	NPD4633	Approved
0.8144	Intermediate Similarity	NPD5225	Approved
0.8144	Intermediate Similarity	NPD5211	Phase 2
0.8132	Intermediate Similarity	NPD4753	Phase 2
0.8125	Intermediate Similarity	NPD4700	Approved
0.8061	Intermediate Similarity	NPD5174	Approved
0.8061	Intermediate Similarity	NPD5175	Approved
0.8041	Intermediate Similarity	NPD5223	Approved
0.798	Intermediate Similarity	NPD5141	Approved
0.7955	Intermediate Similarity	NPD4223	Phase 3
0.7955	Intermediate Similarity	NPD4221	Approved
0.7921	Intermediate Similarity	NPD6899	Approved
0.7921	Intermediate Similarity	NPD6881	Approved
0.79	Intermediate Similarity	NPD5739	Approved
0.79	Intermediate Similarity	NPD7128	Approved
0.79	Intermediate Similarity	NPD6675	Approved
0.79	Intermediate Similarity	NPD6402	Approved
0.7895	Intermediate Similarity	NPD4629	Approved
0.7895	Intermediate Similarity	NPD5210	Approved
0.7889	Intermediate Similarity	NPD5329	Approved
0.7889	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD5697	Approved
0.7802	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD5280	Approved
0.7802	Intermediate Similarity	NPD7521	Approved
0.7802	Intermediate Similarity	NPD7334	Approved
0.7802	Intermediate Similarity	NPD7146	Approved
0.7802	Intermediate Similarity	NPD6684	Approved
0.7802	Intermediate Similarity	NPD6409	Approved
0.7802	Intermediate Similarity	NPD5330	Approved
0.7802	Intermediate Similarity	NPD4694	Approved
0.7789	Intermediate Similarity	NPD7748	Approved
0.7778	Intermediate Similarity	NPD4197	Approved
0.7778	Intermediate Similarity	NPD3668	Phase 3
0.7767	Intermediate Similarity	NPD7290	Approved
0.7767	Intermediate Similarity	NPD6883	Approved
0.7767	Intermediate Similarity	NPD7102	Approved
0.7745	Intermediate Similarity	NPD7320	Approved
0.7745	Intermediate Similarity	NPD4730	Approved
0.7745	Intermediate Similarity	NPD4729	Approved
0.7732	Intermediate Similarity	NPD6083	Phase 2
0.7732	Intermediate Similarity	NPD6084	Phase 2
0.7727	Intermediate Similarity	NPD7525	Registered
0.7723	Intermediate Similarity	NPD4768	Approved
0.7723	Intermediate Similarity	NPD4767	Approved
0.7701	Intermediate Similarity	NPD3617	Approved
0.77	Intermediate Similarity	NPD4754	Approved
0.7692	Intermediate Similarity	NPD6869	Approved
0.7692	Intermediate Similarity	NPD6617	Approved
0.7692	Intermediate Similarity	NPD8130	Phase 1
0.7692	Intermediate Similarity	NPD6650	Approved
0.7692	Intermediate Similarity	NPD6847	Approved
0.7692	Intermediate Similarity	NPD6649	Approved
0.7684	Intermediate Similarity	NPD6399	Phase 3
0.767	Intermediate Similarity	NPD6373	Approved
0.767	Intermediate Similarity	NPD6014	Approved
0.767	Intermediate Similarity	NPD6372	Approved
0.767	Intermediate Similarity	NPD6013	Approved
0.767	Intermediate Similarity	NPD6012	Approved
0.7667	Intermediate Similarity	NPD4788	Approved
0.7653	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD4058	Approved
0.7647	Intermediate Similarity	NPD6926	Approved
0.7647	Intermediate Similarity	NPD6924	Approved
0.7647	Intermediate Similarity	NPD5701	Approved
0.7634	Intermediate Similarity	NPD6903	Approved
0.7634	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6882	Approved
0.7619	Intermediate Similarity	NPD7152	Approved
0.7619	Intermediate Similarity	NPD8297	Approved
0.7619	Intermediate Similarity	NPD7151	Approved
0.7619	Intermediate Similarity	NPD7150	Approved
0.7609	Intermediate Similarity	NPD4689	Approved
0.7609	Intermediate Similarity	NPD4693	Phase 3
0.7609	Intermediate Similarity	NPD4690	Approved
0.7609	Intermediate Similarity	NPD5690	Phase 2
0.7609	Intermediate Similarity	NPD4688	Approved
0.7609	Intermediate Similarity	NPD5205	Approved
0.7609	Intermediate Similarity	NPD4138	Approved
0.7596	Intermediate Similarity	NPD4634	Approved
0.7596	Intermediate Similarity	NPD5247	Approved
0.7596	Intermediate Similarity	NPD5250	Approved
0.7596	Intermediate Similarity	NPD5249	Phase 3
0.7596	Intermediate Similarity	NPD5248	Approved
0.7596	Intermediate Similarity	NPD5251	Approved
0.7579	Intermediate Similarity	NPD5281	Approved
0.7579	Intermediate Similarity	NPD5284	Approved
0.7576	Intermediate Similarity	NPD7640	Approved
0.7576	Intermediate Similarity	NPD7639	Approved
0.7573	Intermediate Similarity	NPD6011	Approved
0.7573	Intermediate Similarity	NPD5168	Approved
0.7573	Intermediate Similarity	NPD5128	Approved
0.7558	Intermediate Similarity	NPD6942	Approved
0.7558	Intermediate Similarity	NPD7339	Approved
0.7551	Intermediate Similarity	NPD7902	Approved
0.7528	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5216	Approved
0.7524	Intermediate Similarity	NPD5217	Approved
0.7524	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD7143	Approved
0.75	Intermediate Similarity	NPD7144	Approved
0.7471	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6933	Approved
0.7447	Intermediate Similarity	NPD5737	Approved
0.7447	Intermediate Similarity	NPD6672	Approved
0.7442	Intermediate Similarity	NPD5733	Approved
0.7442	Intermediate Similarity	NPD4687	Approved
0.7429	Intermediate Similarity	NPD5169	Approved
0.7429	Intermediate Similarity	NPD5135	Approved
0.7429	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4519	Discontinued
0.7419	Intermediate Similarity	NPD4623	Approved
0.7416	Intermediate Similarity	NPD6929	Approved
0.7416	Intermediate Similarity	NPD4195	Approved
0.7416	Intermediate Similarity	NPD7645	Phase 2
0.7412	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6932	Approved
0.7381	Intermediate Similarity	NPD6923	Approved
0.7381	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4137	Phase 3
0.7381	Intermediate Similarity	NPD6922	Approved
0.7358	Intermediate Similarity	NPD5127	Approved
0.7358	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5695	Phase 3
0.7339	Intermediate Similarity	NPD7115	Discovery
0.7333	Intermediate Similarity	NPD6931	Approved
0.7333	Intermediate Similarity	NPD4695	Discontinued
0.7333	Intermediate Similarity	NPD6930	Phase 2
0.7308	Intermediate Similarity	NPD6412	Phase 2
0.7303	Intermediate Similarity	NPD7145	Approved
0.73	Intermediate Similarity	NPD5696	Approved
0.73	Intermediate Similarity	NPD5290	Discontinued
0.7294	Intermediate Similarity	NPD4747	Approved
0.7294	Intermediate Similarity	NPD4691	Approved
0.7292	Intermediate Similarity	NPD4096	Approved
0.7263	Intermediate Similarity	NPD4518	Approved
0.7248	Intermediate Similarity	NPD6868	Approved
0.7245	Intermediate Similarity	NPD7900	Approved
0.7245	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4632	Approved
0.7216	Intermediate Similarity	NPD6411	Approved
0.7216	Intermediate Similarity	NPD8034	Phase 2
0.7216	Intermediate Similarity	NPD8035	Phase 2
0.7209	Intermediate Similarity	NPD5276	Approved
0.7207	Intermediate Similarity	NPD7101	Approved
0.7207	Intermediate Similarity	NPD7100	Approved
0.7191	Intermediate Similarity	NPD5776	Phase 2
0.7191	Intermediate Similarity	NPD6925	Approved
0.7188	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3703	Phase 2
0.7158	Intermediate Similarity	NPD3573	Approved
0.7156	Intermediate Similarity	NPD5167	Approved
0.7143	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD7514	Phase 3
0.7143	Intermediate Similarity	NPD7509	Discontinued
0.7143	Intermediate Similarity	NPD5133	Approved
0.7117	Intermediate Similarity	NPD6335	Approved
0.7113	Intermediate Similarity	NPD5207	Approved
0.7111	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6695	Phase 3
0.7093	Intermediate Similarity	NPD4244	Approved
0.7093	Intermediate Similarity	NPD4245	Approved
0.7091	Intermediate Similarity	NPD6274	Approved
0.7079	Intermediate Similarity	NPD6117	Approved
0.7065	Intermediate Similarity	NPD6902	Approved
0.7045	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5694	Approved
0.7041	Intermediate Similarity	NPD6050	Approved
0.7041	Intermediate Similarity	NPD7637	Suspended
0.7033	Intermediate Similarity	NPD6683	Phase 2
0.7027	Intermediate Similarity	NPD6317	Approved
0.7027	Intermediate Similarity	NPD6009	Approved
0.7021	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6370	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