NPASS Compound

Structure

NPC141292 OpenBabel07101718252D 32 34 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 3.5981 -1.5000 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 -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 -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 -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 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 2.5981 -2.5000 0.0000 C 0 0 1 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 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 -2.5388 -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 5 28 1 0 0 0 0 6 28 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 11 20 2 0 0 0 0 12 21 1 0 0 0 0 13 21 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 22 27 2 0 0 0 0 23 27 1 0 0 0 0 23 31 2 0 0 0 0 24 28 1 0 0 0 0 24 29 1 1 0 0 0 25 29 1 6 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 32 1 1 0 0 0 27 30 1 0 0 0 0 29 7 1 1 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.35
Volume:	506.165
LogP:	6.59
LogD:	5.174
LogS:	-5.903
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	4.551
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.833
MDCK Permeability:	1.847203566285316e-05
Pgp-inhibitor:	0.918
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	0.38

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	95.40021514892578%
Volume Distribution (VD):	1.899
Pgp-substrate:	3.3242154121398926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.339
CYP2C19-inhibitor:	0.349
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.485
CYP2C9-substrate:	0.234
CYP2D6-inhibitor:	0.596
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.564

ADMET: Excretion

Clearance (CL):	9.012
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.632
Human Hepatotoxicity (H-HT):	0.723
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.643
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.937
Carcinogencity:	0.151
Eye Corrosion:	0.004
Eye Irritation:	0.037
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC141292

Natural Product ID:	NPC141292
*Common Name:**	Stelliferin D
IUPAC Name:	(3Z,3aS,5aR,7S,9aR,9bS)-3-[(3E,5E)-6,10-dimethylundeca-3,5,9-trien-2-ylidene]-7-hydroxy-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-2-one
Synonyms:	stelliferin D
Standard InCHIKey:	YSFGMSKQXKVXAR-HXXDOKHASA-N
Standard InCHI:	InChI=1S/C30H46O2/c1-20(2)11-9-12-21(3)13-10-14-22(4)27-23(31)19-25-29(7)18-16-26(32)28(5,6)24(29)15-17-30(25,27)8/h10-11,13-14,24-26,32H,9,12,15-19H2,1-8H3/b14-10+,21-13+,27-22+/t24-,25-,26-,29-,30-/m0/s1
SMILES:	C/C(=CC=CC(=C1/C(=O)C[C@@H]2[C@]1(C)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)O)C)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481848
PubChem CID:	10094698
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
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691710]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	Kubat, Malaysia	1991	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778241]
NPO10924	Stelletta 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
GI50	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	GI50	=	24.0	nM	PMID[485429]
NPT27	Others	Unspecified		GI50	=	18.0	nM	PMID[485429]

☑ 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 NPC141292 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	160
0.1-0.2	896
0.2-0.3	4106
0.3-0.4	12160
0.4-0.5	10992
0.5-0.6	6879
0.6-0.7	4956
0.7-0.8	2248
0.8-0.85	207
0.85-0.9	77
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC310752
0.9878	High Similarity	NPC292491
0.931	High Similarity	NPC299100
0.931	High Similarity	NPC474690
0.9277	High Similarity	NPC470574
0.9205	High Similarity	NPC180950
0.9205	High Similarity	NPC88310
0.9101	High Similarity	NPC301534
0.9101	High Similarity	NPC250757
0.9101	High Similarity	NPC471153
0.908	High Similarity	NPC272746
0.9059	High Similarity	NPC475740
0.9059	High Similarity	NPC58063
0.9	High Similarity	NPC474938
0.9	High Similarity	NPC474785
0.8966	High Similarity	NPC126993
0.8953	High Similarity	NPC471722
0.8953	High Similarity	NPC328539
0.8941	High Similarity	NPC474733
0.8941	High Similarity	NPC474732
0.8941	High Similarity	NPC31564
0.8941	High Similarity	NPC145879
0.8941	High Similarity	NPC72133
0.8941	High Similarity	NPC474778
0.8929	High Similarity	NPC214043
0.8929	High Similarity	NPC85774
0.8901	High Similarity	NPC108368
0.8901	High Similarity	NPC57079
0.8901	High Similarity	NPC103051
0.8876	High Similarity	NPC209662
0.8864	High Similarity	NPC475806
0.8851	High Similarity	NPC473999
0.8851	High Similarity	NPC1015
0.8851	High Similarity	NPC275740
0.8851	High Similarity	NPC309603
0.8851	High Similarity	NPC86319
0.8851	High Similarity	NPC31985
0.8837	High Similarity	NPC136548
0.8804	High Similarity	NPC266955
0.8778	High Similarity	NPC280725
0.8764	High Similarity	NPC12722
0.8764	High Similarity	NPC475255
0.8764	High Similarity	NPC134826
0.875	High Similarity	NPC474842
0.875	High Similarity	NPC85173
0.875	High Similarity	NPC48010
0.875	High Similarity	NPC475965
0.875	High Similarity	NPC191684
0.8736	High Similarity	NPC131470
0.8736	High Similarity	NPC193360
0.8736	High Similarity	NPC143767
0.8721	High Similarity	NPC475022
0.8721	High Similarity	NPC222613
0.8721	High Similarity	NPC118648
0.871	High Similarity	NPC115899
0.871	High Similarity	NPC282524
0.8706	High Similarity	NPC329043
0.8706	High Similarity	NPC58841
0.8706	High Similarity	NPC321187
0.8706	High Similarity	NPC473246
0.8706	High Similarity	NPC221758
0.8706	High Similarity	NPC59453
0.8706	High Similarity	NPC161423
0.8706	High Similarity	NPC227064
0.869	High Similarity	NPC151519
0.8667	High Similarity	NPC8993
0.8667	High Similarity	NPC111015
0.8667	High Similarity	NPC196485
0.8667	High Similarity	NPC245972
0.8652	High Similarity	NPC185936
0.8652	High Similarity	NPC168027
0.8652	High Similarity	NPC473998
0.8636	High Similarity	NPC84271
0.8636	High Similarity	NPC268406
0.8636	High Similarity	NPC102414
0.8636	High Similarity	NPC77168
0.8636	High Similarity	NPC119416
0.8636	High Similarity	NPC186688
0.8636	High Similarity	NPC26959
0.8636	High Similarity	NPC128496
0.8621	High Similarity	NPC93778
0.8621	High Similarity	NPC142361
0.8621	High Similarity	NPC474684
0.8617	High Similarity	NPC155332
0.8617	High Similarity	NPC114540
0.8617	High Similarity	NPC32577
0.8605	High Similarity	NPC469948
0.8605	High Similarity	NPC197823
0.8602	High Similarity	NPC35751
0.8587	High Similarity	NPC108078
0.8571	High Similarity	NPC271195
0.8571	High Similarity	NPC259286
0.8571	High Similarity	NPC121984
0.8556	High Similarity	NPC69454
0.8554	High Similarity	NPC229204
0.8539	High Similarity	NPC183283
0.8537	High Similarity	NPC197659
0.8526	High Similarity	NPC475050
0.8523	High Similarity	NPC471724
0.8523	High Similarity	NPC474677
0.8523	High Similarity	NPC472802
0.8506	High Similarity	NPC471737
0.8506	High Similarity	NPC327115
0.8506	High Similarity	NPC94755
0.8506	High Similarity	NPC473168
0.8506	High Similarity	NPC51014
0.8506	High Similarity	NPC158393
0.8495	Intermediate Similarity	NPC191565
0.8488	Intermediate Similarity	NPC82902
0.8488	Intermediate Similarity	NPC237712
0.8488	Intermediate Similarity	NPC33913
0.8488	Intermediate Similarity	NPC472265
0.8478	Intermediate Similarity	NPC249954
0.8471	Intermediate Similarity	NPC48362
0.8462	Intermediate Similarity	NPC473435
0.8462	Intermediate Similarity	NPC49670
0.8462	Intermediate Similarity	NPC473172
0.8462	Intermediate Similarity	NPC473431
0.8462	Intermediate Similarity	NPC471207
0.8462	Intermediate Similarity	NPC471078
0.8462	Intermediate Similarity	NPC473280
0.8452	Intermediate Similarity	NPC164999
0.8452	Intermediate Similarity	NPC2482
0.8444	Intermediate Similarity	NPC233116
0.8444	Intermediate Similarity	NPC473167
0.8444	Intermediate Similarity	NPC155304
0.8444	Intermediate Similarity	NPC63748
0.8444	Intermediate Similarity	NPC19114
0.8427	Intermediate Similarity	NPC477943
0.8427	Intermediate Similarity	NPC32830
0.8427	Intermediate Similarity	NPC475921
0.8427	Intermediate Similarity	NPC474245
0.8427	Intermediate Similarity	NPC474704
0.8409	Intermediate Similarity	NPC233836
0.8409	Intermediate Similarity	NPC287079
0.8409	Intermediate Similarity	NPC187376
0.8409	Intermediate Similarity	NPC475772
0.8409	Intermediate Similarity	NPC159046
0.8391	Intermediate Similarity	NPC76518
0.8391	Intermediate Similarity	NPC133954
0.8391	Intermediate Similarity	NPC471224
0.8391	Intermediate Similarity	NPC22133
0.8391	Intermediate Similarity	NPC474218
0.8372	Intermediate Similarity	NPC64600
0.8372	Intermediate Similarity	NPC312480
0.8372	Intermediate Similarity	NPC475726
0.8372	Intermediate Similarity	NPC278648
0.8372	Intermediate Similarity	NPC476082
0.8372	Intermediate Similarity	NPC472743
0.837	Intermediate Similarity	NPC473170
0.837	Intermediate Similarity	NPC139459
0.8353	Intermediate Similarity	NPC136150
0.8353	Intermediate Similarity	NPC473217
0.8352	Intermediate Similarity	NPC109305
0.8352	Intermediate Similarity	NPC250575
0.8352	Intermediate Similarity	NPC474736
0.8351	Intermediate Similarity	NPC266570
0.8333	Intermediate Similarity	NPC129913
0.8333	Intermediate Similarity	NPC72151
0.8333	Intermediate Similarity	NPC474113
0.8315	Intermediate Similarity	NPC158778
0.8315	Intermediate Similarity	NPC206060
0.8315	Intermediate Similarity	NPC328313
0.8315	Intermediate Similarity	NPC53911
0.8313	Intermediate Similarity	NPC472746
0.8298	Intermediate Similarity	NPC114274
0.8295	Intermediate Similarity	NPC472986
0.8295	Intermediate Similarity	NPC472985
0.8295	Intermediate Similarity	NPC469994
0.8295	Intermediate Similarity	NPC475862
0.8295	Intermediate Similarity	NPC155011
0.8295	Intermediate Similarity	NPC20688
0.8295	Intermediate Similarity	NPC89077
0.8295	Intermediate Similarity	NPC74363
0.8295	Intermediate Similarity	NPC28252
0.8295	Intermediate Similarity	NPC179591
0.8295	Intermediate Similarity	NPC55309
0.8295	Intermediate Similarity	NPC213412
0.8295	Intermediate Similarity	NPC94666
0.828	Intermediate Similarity	NPC78473
0.828	Intermediate Similarity	NPC473164
0.828	Intermediate Similarity	NPC122324
0.828	Intermediate Similarity	NPC151725
0.828	Intermediate Similarity	NPC192428
0.828	Intermediate Similarity	NPC106425
0.8276	Intermediate Similarity	NPC475745
0.8276	Intermediate Similarity	NPC474482
0.8265	Intermediate Similarity	NPC473284
0.8265	Intermediate Similarity	NPC329048
0.8265	Intermediate Similarity	NPC330011
0.8261	Intermediate Similarity	NPC473162
0.8261	Intermediate Similarity	NPC474328
0.8261	Intermediate Similarity	NPC166906
0.8261	Intermediate Similarity	NPC469406
0.8242	Intermediate Similarity	NPC86266
0.8242	Intermediate Similarity	NPC474018
0.8242	Intermediate Similarity	NPC65120
0.8242	Intermediate Similarity	NPC301244
0.8242	Intermediate Similarity	NPC110657
0.8242	Intermediate Similarity	NPC4036

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 NPC141292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1136
0.2-0.3	3746
0.3-0.4	2758
0.4-0.5	830
0.5-0.6	221
0.6-0.7	118
0.7-0.8	163
0.8-0.85	23
0.85-0.9	10
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD3618	Phase 1
0.908	High Similarity	NPD6079	Approved
0.907	High Similarity	NPD5328	Approved
0.8706	High Similarity	NPD4786	Approved
0.8706	High Similarity	NPD3666	Approved
0.8706	High Similarity	NPD3133	Approved
0.8706	High Similarity	NPD3665	Phase 1
0.869	High Similarity	NPD3667	Approved
0.8556	High Similarity	NPD4202	Approved
0.8506	High Similarity	NPD5279	Phase 3
0.8478	Intermediate Similarity	NPD5222	Approved
0.8478	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD5221	Approved
0.8387	Intermediate Similarity	NPD5173	Approved
0.828	Intermediate Similarity	NPD4697	Phase 3
0.8242	Intermediate Similarity	NPD7515	Phase 2
0.8211	Intermediate Similarity	NPD4696	Approved
0.8211	Intermediate Similarity	NPD5286	Approved
0.8211	Intermediate Similarity	NPD5285	Approved
0.8191	Intermediate Similarity	NPD4755	Approved
0.8125	Intermediate Similarity	NPD5223	Approved
0.8046	Intermediate Similarity	NPD4223	Phase 3
0.8046	Intermediate Similarity	NPD4221	Approved
0.8041	Intermediate Similarity	NPD5225	Approved
0.8041	Intermediate Similarity	NPD5211	Phase 2
0.8041	Intermediate Similarity	NPD4633	Approved
0.8041	Intermediate Similarity	NPD5226	Approved
0.8041	Intermediate Similarity	NPD5224	Approved
0.8022	Intermediate Similarity	NPD4753	Phase 2
0.8021	Intermediate Similarity	NPD4700	Approved
0.7978	Intermediate Similarity	NPD5329	Approved
0.7978	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5174	Approved
0.7959	Intermediate Similarity	NPD5175	Approved
0.7889	Intermediate Similarity	NPD7521	Approved
0.7889	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD4694	Approved
0.7889	Intermediate Similarity	NPD7146	Approved
0.7889	Intermediate Similarity	NPD5280	Approved
0.7889	Intermediate Similarity	NPD5330	Approved
0.7889	Intermediate Similarity	NPD6409	Approved
0.7889	Intermediate Similarity	NPD7334	Approved
0.7889	Intermediate Similarity	NPD6684	Approved
0.7879	Intermediate Similarity	NPD5141	Approved
0.7872	Intermediate Similarity	NPD7748	Approved
0.7865	Intermediate Similarity	NPD3668	Phase 3
0.7865	Intermediate Similarity	NPD4197	Approved
0.7822	Intermediate Similarity	NPD6899	Approved
0.7822	Intermediate Similarity	NPD6881	Approved
0.7816	Intermediate Similarity	NPD7525	Registered
0.78	Intermediate Similarity	NPD5739	Approved
0.78	Intermediate Similarity	NPD7128	Approved
0.78	Intermediate Similarity	NPD6675	Approved
0.78	Intermediate Similarity	NPD6402	Approved
0.7791	Intermediate Similarity	NPD3617	Approved
0.7789	Intermediate Similarity	NPD5210	Approved
0.7789	Intermediate Similarity	NPD4629	Approved
0.7778	Intermediate Similarity	NPD4754	Approved
0.7766	Intermediate Similarity	NPD6399	Phase 3
0.7753	Intermediate Similarity	NPD4788	Approved
0.7738	Intermediate Similarity	NPD6926	Approved
0.7738	Intermediate Similarity	NPD4058	Approved
0.7738	Intermediate Similarity	NPD6924	Approved
0.7732	Intermediate Similarity	NPD7638	Approved
0.7723	Intermediate Similarity	NPD5697	Approved
0.7717	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6903	Approved
0.7711	Intermediate Similarity	NPD7152	Approved
0.7711	Intermediate Similarity	NPD7151	Approved
0.7711	Intermediate Similarity	NPD7150	Approved
0.7692	Intermediate Similarity	NPD4690	Approved
0.7692	Intermediate Similarity	NPD4693	Phase 3
0.7692	Intermediate Similarity	NPD5205	Approved
0.7692	Intermediate Similarity	NPD5690	Phase 2
0.7692	Intermediate Similarity	NPD4689	Approved
0.7692	Intermediate Similarity	NPD4138	Approved
0.7692	Intermediate Similarity	NPD4688	Approved
0.767	Intermediate Similarity	NPD6883	Approved
0.767	Intermediate Similarity	NPD7102	Approved
0.767	Intermediate Similarity	NPD7290	Approved
0.766	Intermediate Similarity	NPD5281	Approved
0.766	Intermediate Similarity	NPD5284	Approved
0.7653	Intermediate Similarity	NPD7640	Approved
0.7653	Intermediate Similarity	NPD7639	Approved
0.7647	Intermediate Similarity	NPD7320	Approved
0.7647	Intermediate Similarity	NPD4730	Approved
0.7647	Intermediate Similarity	NPD4729	Approved
0.7647	Intermediate Similarity	NPD6011	Approved
0.7647	Intermediate Similarity	NPD5168	Approved
0.7647	Intermediate Similarity	NPD6942	Approved
0.7647	Intermediate Similarity	NPD7339	Approved
0.7629	Intermediate Similarity	NPD6084	Phase 2
0.7629	Intermediate Similarity	NPD7902	Approved
0.7629	Intermediate Similarity	NPD6083	Phase 2
0.7624	Intermediate Similarity	NPD4767	Approved
0.7624	Intermediate Similarity	NPD4768	Approved
0.7614	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6649	Approved
0.7596	Intermediate Similarity	NPD6617	Approved
0.7596	Intermediate Similarity	NPD8130	Phase 1
0.7596	Intermediate Similarity	NPD6847	Approved
0.7596	Intermediate Similarity	NPD6650	Approved
0.7596	Intermediate Similarity	NPD6869	Approved
0.759	Intermediate Similarity	NPD7144	Approved
0.759	Intermediate Similarity	NPD7143	Approved
0.7573	Intermediate Similarity	NPD6012	Approved
0.7573	Intermediate Similarity	NPD6014	Approved
0.7573	Intermediate Similarity	NPD6013	Approved
0.7573	Intermediate Similarity	NPD6373	Approved
0.7573	Intermediate Similarity	NPD6372	Approved
0.7558	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6933	Approved
0.7549	Intermediate Similarity	NPD5701	Approved
0.7529	Intermediate Similarity	NPD4687	Approved
0.7529	Intermediate Similarity	NPD5733	Approved
0.7527	Intermediate Similarity	NPD6672	Approved
0.7527	Intermediate Similarity	NPD5737	Approved
0.7524	Intermediate Similarity	NPD6882	Approved
0.7524	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5248	Approved
0.75	Intermediate Similarity	NPD5247	Approved
0.75	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD5250	Approved
0.75	Intermediate Similarity	NPD5249	Phase 3
0.75	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD5169	Approved
0.75	Intermediate Similarity	NPD5251	Approved
0.75	Intermediate Similarity	NPD4634	Approved
0.75	Intermediate Similarity	NPD5135	Approved
0.7476	Intermediate Similarity	NPD5128	Approved
0.747	Intermediate Similarity	NPD4137	Phase 3
0.747	Intermediate Similarity	NPD6923	Approved
0.747	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6922	Approved
0.7429	Intermediate Similarity	NPD5215	Approved
0.7429	Intermediate Similarity	NPD5216	Approved
0.7429	Intermediate Similarity	NPD5127	Approved
0.7429	Intermediate Similarity	NPD5217	Approved
0.7429	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4695	Discontinued
0.7381	Intermediate Similarity	NPD4691	Approved
0.7381	Intermediate Similarity	NPD4747	Approved
0.7374	Intermediate Similarity	NPD5290	Discontinued
0.7368	Intermediate Similarity	NPD4096	Approved
0.734	Intermediate Similarity	NPD4518	Approved
0.732	Intermediate Similarity	NPD7900	Approved
0.732	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6868	Approved
0.7303	Intermediate Similarity	NPD7645	Phase 2
0.7303	Intermediate Similarity	NPD6929	Approved
0.7294	Intermediate Similarity	NPD5276	Approved
0.7292	Intermediate Similarity	NPD8034	Phase 2
0.7292	Intermediate Similarity	NPD8035	Phase 2
0.729	Intermediate Similarity	NPD4632	Approved
0.7273	Intermediate Similarity	NPD6932	Approved
0.7263	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7245	Intermediate Similarity	NPD5695	Phase 3
0.7245	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3703	Phase 2
0.7234	Intermediate Similarity	NPD3573	Approved
0.7222	Intermediate Similarity	NPD5167	Approved
0.7222	Intermediate Similarity	NPD7509	Discontinued
0.7222	Intermediate Similarity	NPD6930	Phase 2
0.7222	Intermediate Similarity	NPD6931	Approved
0.7216	Intermediate Similarity	NPD5133	Approved
0.7212	Intermediate Similarity	NPD6412	Phase 2
0.72	Intermediate Similarity	NPD5696	Approved
0.7195	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7145	Approved
0.7188	Intermediate Similarity	NPD5207	Approved
0.7182	Intermediate Similarity	NPD6335	Approved
0.7176	Intermediate Similarity	NPD4245	Approved
0.7176	Intermediate Similarity	NPD4244	Approved
0.7159	Intermediate Similarity	NPD6117	Approved
0.7126	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7100	Approved
0.7117	Intermediate Similarity	NPD7101	Approved
0.7113	Intermediate Similarity	NPD6050	Approved
0.7113	Intermediate Similarity	NPD5694	Approved
0.7113	Intermediate Similarity	NPD6411	Approved
0.7091	Intermediate Similarity	NPD6009	Approved
0.7091	Intermediate Similarity	NPD6317	Approved
0.7083	Intermediate Similarity	NPD6904	Approved
0.7083	Intermediate Similarity	NPD6080	Approved
0.7083	Intermediate Similarity	NPD6673	Approved
0.7079	Intermediate Similarity	NPD5776	Phase 2
0.7079	Intermediate Similarity	NPD6116	Phase 1
0.7079	Intermediate Similarity	NPD6925	Approved
0.7059	Intermediate Similarity	NPD3698	Phase 2
0.7054	Intermediate Similarity	NPD6054	Approved
0.7045	Intermediate Similarity	NPD8264	Approved
0.7033	Intermediate Similarity	NPD7514	Phase 3
0.7027	Intermediate Similarity	NPD6314	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