NPASS Compound

Structure

NPC301534 OpenBabel07101718322D 34 36 0 0 1 0 0 0 0 0999 V2000 3.5254 -2.6270 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 6.0997 -4.9449 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 2.9074 -0.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4817 -3.0428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8855 -0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1727 -2.0917 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 6.4598 -3.2507 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 4.1945 -1.8838 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 6.7688 -4.2017 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 7.7470 -4.4097 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 8.0560 -5.3607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4161 -3.6665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 10 1 0 0 0 0 8 12 2 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 18 24 1 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 22 26 1 0 0 0 0 22 31 2 0 0 0 0 23 28 1 0 0 0 0 23 29 1 1 0 0 0 24 29 1 6 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 25 32 1 1 0 0 0 26 30 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 29 6 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.31
Volume:	518.472
LogP:	4.475
LogD:	4.09
LogS:	-4.675
# Rotatable Bonds:	5
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	4.69
Fsp3:	0.6
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:	-5.201
MDCK Permeability:	2.5696612283354625e-05
Pgp-inhibitor:	0.853
Pgp-substrate:	0.847
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.551
Plasma Protein Binding (PPB):	95.22775268554688%
Volume Distribution (VD):	0.539
Pgp-substrate:	5.831271648406982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.202
CYP1A2-substrate:	0.633
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.568
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.689
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.47
CYP3A4-substrate:	0.329

ADMET: Excretion

Clearance (CL):	1.431
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.146
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.827
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.917
Carcinogencity:	0.286
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC301534

Natural Product ID:	NPC301534
*Common Name:**	Stellettin M
IUPAC Name:	(2E,4E,6E,8E,10Z)-10-[(3aS,5aR,7S,9aR,9bS)-7-hydroxy-3a,6,6,9a-tetramethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid
Synonyms:	stellettin M
Standard InCHIKey:	HQKNXSLBDXDYEF-BPBRLBPSSA-N
Standard InCHI:	InChI=1S/C30H42O4/c1-19(11-9-13-21(3)27(33)34)10-8-12-20(2)26-22(31)18-24-29(6)17-15-25(32)28(4,5)23(29)14-16-30(24,26)7/h8-13,23-25,32H,14-18H2,1-7H3,(H,33,34)/b11-9+,12-8+,19-10+,21-13+,26-20+/t23-,24-,25-,29-,30-/m0/s1
SMILES:	C/C(=CC=CC(=C1/C(=O)C[C@H]2[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@]12C)O)C)/C=C/C=C(C)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228657
PubChem CID:	16756778
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
NPO33155	stelletta tenuis	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17604394]
NPO33155	stelletta tenuis	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7807129]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	34000.0	nM	PMID[476119]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	90000.0	nM	PMID[476119]
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	2100.0	nM	PMID[476119]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	42000.0	nM	PMID[476119]

☑ 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 NPC301534 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	170
0.1-0.2	846
0.2-0.3	3462
0.3-0.4	8381
0.4-0.5	13536
0.5-0.6	7139
0.6-0.7	5816
0.7-0.8	2934
0.8-0.85	320
0.85-0.9	64
0.9-0.95	23
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC250757
0.957	High Similarity	NPC282524
0.9565	High Similarity	NPC108368
0.9565	High Similarity	NPC57079
0.9556	High Similarity	NPC299100
0.9462	High Similarity	NPC266955
0.9451	High Similarity	NPC180950
0.9362	High Similarity	NPC115899
0.9341	High Similarity	NPC474690
0.9239	High Similarity	NPC88310
0.9167	High Similarity	NPC72151
0.9167	High Similarity	NPC475050
0.914	High Similarity	NPC471153
0.9121	High Similarity	NPC473986
0.9121	High Similarity	NPC474018
0.9101	High Similarity	NPC141292
0.9062	High Similarity	NPC114540
0.9062	High Similarity	NPC155332
0.9062	High Similarity	NPC32577
0.9062	High Similarity	NPC320447
0.9043	High Similarity	NPC474785
0.9043	High Similarity	NPC253826
0.9043	High Similarity	NPC474938
0.9011	High Similarity	NPC475965
0.9011	High Similarity	NPC474842
0.9	High Similarity	NPC104560
0.9	High Similarity	NPC292491
0.9	High Similarity	NPC310752
0.898	High Similarity	NPC266570
0.8947	High Similarity	NPC103051
0.8925	High Similarity	NPC469406
0.8889	High Similarity	NPC473284
0.8854	High Similarity	NPC35751
0.8842	High Similarity	NPC108078
0.883	High Similarity	NPC476174
0.8817	High Similarity	NPC214697
0.8788	High Similarity	NPC189863
0.8776	High Similarity	NPC473283
0.8776	High Similarity	NPC475526
0.8776	High Similarity	NPC329345
0.8763	High Similarity	NPC118174
0.8763	High Similarity	NPC476240
0.8763	High Similarity	NPC224720
0.8763	High Similarity	NPC476223
0.875	High Similarity	NPC235464
0.875	High Similarity	NPC166745
0.8737	High Similarity	NPC472941
0.8737	High Similarity	NPC456
0.8723	High Similarity	NPC8993
0.871	High Similarity	NPC473998
0.871	High Similarity	NPC475806
0.871	High Similarity	NPC212948
0.87	High Similarity	NPC329048
0.87	High Similarity	NPC330011
0.8696	High Similarity	NPC309603
0.8696	High Similarity	NPC214387
0.8696	High Similarity	NPC262858
0.8696	High Similarity	NPC472240
0.8696	High Similarity	NPC473999
0.8673	High Similarity	NPC293753
0.8667	High Similarity	NPC109528
0.866	High Similarity	NPC470074
0.866	High Similarity	NPC476274
0.8652	High Similarity	NPC279639
0.8652	High Similarity	NPC3856
0.8646	High Similarity	NPC110937
0.8646	High Similarity	NPC99726
0.8646	High Similarity	NPC320306
0.8646	High Similarity	NPC2049
0.8632	High Similarity	NPC139459
0.8617	High Similarity	NPC476304
0.8602	High Similarity	NPC477147
0.8602	High Similarity	NPC48010
0.8602	High Similarity	NPC477149
0.8571	High Similarity	NPC194028
0.8571	High Similarity	NPC168319
0.8557	High Similarity	NPC48647
0.8557	High Similarity	NPC478056
0.8557	High Similarity	NPC114274
0.8557	High Similarity	NPC471717
0.8544	High Similarity	NPC474315
0.8542	High Similarity	NPC122324
0.8542	High Similarity	NPC29152
0.8542	High Similarity	NPC151725
0.8542	High Similarity	NPC249954
0.8542	High Similarity	NPC106425
0.8539	High Similarity	NPC469804
0.8539	High Similarity	NPC469805
0.8539	High Similarity	NPC469799
0.8539	High Similarity	NPC469806
0.8529	High Similarity	NPC475065
0.8526	High Similarity	NPC476186
0.8526	High Similarity	NPC49670
0.8526	High Similarity	NPC473431
0.8526	High Similarity	NPC471078
0.8526	High Similarity	NPC473280
0.8526	High Similarity	NPC473435
0.8511	High Similarity	NPC272746
0.8511	High Similarity	NPC204341
0.8511	High Similarity	NPC74296
0.8511	High Similarity	NPC110923
0.8495	Intermediate Similarity	NPC475921
0.8495	Intermediate Similarity	NPC262043
0.8495	Intermediate Similarity	NPC77168
0.8495	Intermediate Similarity	NPC102414
0.8495	Intermediate Similarity	NPC66344
0.8495	Intermediate Similarity	NPC474704
0.8495	Intermediate Similarity	NPC146554
0.8495	Intermediate Similarity	NPC84271
0.8495	Intermediate Similarity	NPC36668
0.8495	Intermediate Similarity	NPC128496
0.8495	Intermediate Similarity	NPC118011
0.8495	Intermediate Similarity	NPC472983
0.8485	Intermediate Similarity	NPC234892
0.8485	Intermediate Similarity	NPC136289
0.8478	Intermediate Similarity	NPC474684
0.8478	Intermediate Similarity	NPC236618
0.8478	Intermediate Similarity	NPC142361
0.8469	Intermediate Similarity	NPC327431
0.8469	Intermediate Similarity	NPC287833
0.8469	Intermediate Similarity	NPC201406
0.8462	Intermediate Similarity	NPC470574
0.8462	Intermediate Similarity	NPC475970
0.8454	Intermediate Similarity	NPC156546
0.8454	Intermediate Similarity	NPC141401
0.8444	Intermediate Similarity	NPC97913
0.8444	Intermediate Similarity	NPC79945
0.8438	Intermediate Similarity	NPC174948
0.8438	Intermediate Similarity	NPC173875
0.8438	Intermediate Similarity	NPC259286
0.8438	Intermediate Similarity	NPC271195
0.8438	Intermediate Similarity	NPC318282
0.8438	Intermediate Similarity	NPC469995
0.8431	Intermediate Similarity	NPC475418
0.8431	Intermediate Similarity	NPC318363
0.8431	Intermediate Similarity	NPC473482
0.8421	Intermediate Similarity	NPC69454
0.8421	Intermediate Similarity	NPC38232
0.8421	Intermediate Similarity	NPC139692
0.8421	Intermediate Similarity	NPC474736
0.8421	Intermediate Similarity	NPC472871
0.8421	Intermediate Similarity	NPC109305
0.8404	Intermediate Similarity	NPC469400
0.8404	Intermediate Similarity	NPC126993
0.84	Intermediate Similarity	NPC112009
0.84	Intermediate Similarity	NPC476237
0.8387	Intermediate Similarity	NPC48107
0.8387	Intermediate Similarity	NPC472870
0.8387	Intermediate Similarity	NPC7280
0.8387	Intermediate Similarity	NPC117122
0.8387	Intermediate Similarity	NPC229612
0.8384	Intermediate Similarity	NPC81530
0.8384	Intermediate Similarity	NPC99411
0.8384	Intermediate Similarity	NPC472924
0.837	Intermediate Similarity	NPC82979
0.837	Intermediate Similarity	NPC473226
0.837	Intermediate Similarity	NPC322159
0.837	Intermediate Similarity	NPC472869
0.837	Intermediate Similarity	NPC186975
0.8367	Intermediate Similarity	NPC197386
0.8367	Intermediate Similarity	NPC186810
0.8367	Intermediate Similarity	NPC316598
0.8352	Intermediate Similarity	NPC19849
0.8352	Intermediate Similarity	NPC165064
0.8352	Intermediate Similarity	NPC302360
0.8352	Intermediate Similarity	NPC164577
0.8352	Intermediate Similarity	NPC472864
0.8351	Intermediate Similarity	NPC114743
0.8351	Intermediate Similarity	NPC242848
0.8351	Intermediate Similarity	NPC134072
0.8351	Intermediate Similarity	NPC7124
0.8351	Intermediate Similarity	NPC328371
0.8351	Intermediate Similarity	NPC195366
0.8351	Intermediate Similarity	NPC234993
0.8351	Intermediate Similarity	NPC190713
0.8333	Intermediate Similarity	NPC166906
0.8333	Intermediate Similarity	NPC279410
0.8333	Intermediate Similarity	NPC472925
0.8333	Intermediate Similarity	NPC119562
0.8333	Intermediate Similarity	NPC2524
0.8317	Intermediate Similarity	NPC472868
0.8316	Intermediate Similarity	NPC470113
0.8316	Intermediate Similarity	NPC63748
0.8316	Intermediate Similarity	NPC158030
0.8316	Intermediate Similarity	NPC189520
0.8316	Intermediate Similarity	NPC86266
0.8316	Intermediate Similarity	NPC65120
0.8316	Intermediate Similarity	NPC145067
0.8316	Intermediate Similarity	NPC212301
0.8316	Intermediate Similarity	NPC110657
0.8316	Intermediate Similarity	NPC472978
0.8316	Intermediate Similarity	NPC476187
0.8316	Intermediate Similarity	NPC233116
0.8316	Intermediate Similarity	NPC4036
0.8316	Intermediate Similarity	NPC233455
0.8315	Intermediate Similarity	NPC469797
0.8315	Intermediate Similarity	NPC281880
0.8315	Intermediate Similarity	NPC469798
0.8298	Intermediate Similarity	NPC310236
0.8298	Intermediate Similarity	NPC472973

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 NPC301534 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	1064
0.2-0.3	3352
0.3-0.4	2900
0.4-0.5	1087
0.5-0.6	251
0.6-0.7	162
0.7-0.8	166
0.8-0.85	22
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8511	High Similarity	NPD6079	Approved
0.837	Intermediate Similarity	NPD3618	Phase 1
0.8316	Intermediate Similarity	NPD7515	Phase 2
0.8298	Intermediate Similarity	NPD5328	Approved
0.8283	Intermediate Similarity	NPD7639	Approved
0.8283	Intermediate Similarity	NPD7640	Approved
0.8182	Intermediate Similarity	NPD7638	Approved
0.8163	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD5221	Approved
0.8163	Intermediate Similarity	NPD5222	Approved
0.8119	Intermediate Similarity	NPD5211	Phase 2
0.8081	Intermediate Similarity	NPD5173	Approved
0.8077	Intermediate Similarity	NPD6899	Approved
0.8077	Intermediate Similarity	NPD6881	Approved
0.7982	Intermediate Similarity	NPD7115	Discovery
0.7981	Intermediate Similarity	NPD5697	Approved
0.7961	Intermediate Similarity	NPD5141	Approved
0.7959	Intermediate Similarity	NPD7748	Approved
0.7957	Intermediate Similarity	NPD3665	Phase 1
0.7957	Intermediate Similarity	NPD3666	Approved
0.7957	Intermediate Similarity	NPD3133	Approved
0.7957	Intermediate Similarity	NPD4786	Approved
0.7935	Intermediate Similarity	NPD3667	Approved
0.7925	Intermediate Similarity	NPD6883	Approved
0.7925	Intermediate Similarity	NPD7290	Approved
0.7925	Intermediate Similarity	NPD7102	Approved
0.7921	Intermediate Similarity	NPD5285	Approved
0.7921	Intermediate Similarity	NPD5286	Approved
0.7921	Intermediate Similarity	NPD4696	Approved
0.7905	Intermediate Similarity	NPD6011	Approved
0.7889	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6402	Approved
0.7885	Intermediate Similarity	NPD5739	Approved
0.7885	Intermediate Similarity	NPD7128	Approved
0.7885	Intermediate Similarity	NPD6675	Approved
0.7872	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6399	Phase 3
0.7857	Intermediate Similarity	NPD4202	Approved
0.785	Intermediate Similarity	NPD6650	Approved
0.785	Intermediate Similarity	NPD6617	Approved
0.785	Intermediate Similarity	NPD6649	Approved
0.785	Intermediate Similarity	NPD6869	Approved
0.785	Intermediate Similarity	NPD8130	Phase 1
0.785	Intermediate Similarity	NPD6847	Approved
0.7843	Intermediate Similarity	NPD5223	Approved
0.783	Intermediate Similarity	NPD6013	Approved
0.783	Intermediate Similarity	NPD6012	Approved
0.783	Intermediate Similarity	NPD6014	Approved
0.78	Intermediate Similarity	NPD4697	Phase 3
0.7789	Intermediate Similarity	NPD6409	Approved
0.7789	Intermediate Similarity	NPD6684	Approved
0.7789	Intermediate Similarity	NPD7334	Approved
0.7789	Intermediate Similarity	NPD7521	Approved
0.7789	Intermediate Similarity	NPD5279	Phase 3
0.7789	Intermediate Similarity	NPD5330	Approved
0.7789	Intermediate Similarity	NPD7146	Approved
0.7778	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD8297	Approved
0.7767	Intermediate Similarity	NPD5224	Approved
0.7767	Intermediate Similarity	NPD5226	Approved
0.7767	Intermediate Similarity	NPD4633	Approved
0.7767	Intermediate Similarity	NPD5225	Approved
0.7755	Intermediate Similarity	NPD5284	Approved
0.7755	Intermediate Similarity	NPD5281	Approved
0.7736	Intermediate Similarity	NPD7320	Approved
0.7723	Intermediate Similarity	NPD6083	Phase 2
0.7723	Intermediate Similarity	NPD7902	Approved
0.7723	Intermediate Similarity	NPD4755	Approved
0.7723	Intermediate Similarity	NPD6084	Phase 2
0.7692	Intermediate Similarity	NPD5174	Approved
0.7692	Intermediate Similarity	NPD5175	Approved
0.7684	Intermediate Similarity	NPD5363	Approved
0.7664	Intermediate Similarity	NPD6372	Approved
0.7664	Intermediate Similarity	NPD6373	Approved
0.7653	Intermediate Similarity	NPD5785	Approved
0.7647	Intermediate Similarity	NPD4225	Approved
0.7642	Intermediate Similarity	NPD5701	Approved
0.7629	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6672	Approved
0.7629	Intermediate Similarity	NPD5737	Approved
0.7629	Intermediate Similarity	NPD6903	Approved
0.7604	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7632	Discontinued
0.7576	Intermediate Similarity	NPD7637	Suspended
0.7573	Intermediate Similarity	NPD4700	Approved
0.7568	Intermediate Similarity	NPD6868	Approved
0.7553	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4753	Phase 2
0.7545	Intermediate Similarity	NPD4632	Approved
0.7525	Intermediate Similarity	NPD5210	Approved
0.7525	Intermediate Similarity	NPD4629	Approved
0.7523	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1694	Approved
0.7434	Intermediate Similarity	NPD6335	Approved
0.7426	Intermediate Similarity	NPD7900	Approved
0.7426	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4519	Discontinued
0.7423	Intermediate Similarity	NPD4623	Approved
0.7407	Intermediate Similarity	NPD4730	Approved
0.7407	Intermediate Similarity	NPD5168	Approved
0.7407	Intermediate Similarity	NPD4729	Approved
0.7404	Intermediate Similarity	NPD6404	Discontinued
0.74	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD8034	Phase 2
0.7396	Intermediate Similarity	NPD3668	Phase 3
0.7374	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4221	Approved
0.7368	Intermediate Similarity	NPD7100	Approved
0.7368	Intermediate Similarity	NPD4223	Phase 3
0.7368	Intermediate Similarity	NPD7101	Approved
0.7368	Intermediate Similarity	NPD4270	Approved
0.7368	Intermediate Similarity	NPD4269	Approved
0.7358	Intermediate Similarity	NPD4754	Approved
0.7353	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5695	Phase 3
0.7347	Intermediate Similarity	NPD3573	Approved
0.7345	Intermediate Similarity	NPD6317	Approved
0.7345	Intermediate Similarity	NPD6009	Approved
0.734	Intermediate Similarity	NPD7525	Registered
0.7327	Intermediate Similarity	NPD5779	Approved
0.7327	Intermediate Similarity	NPD5778	Approved
0.732	Intermediate Similarity	NPD5329	Approved
0.7308	Intermediate Similarity	NPD5696	Approved
0.7292	Intermediate Similarity	NPD4788	Approved
0.7292	Intermediate Similarity	NPD5362	Discontinued
0.7283	Intermediate Similarity	NPD6117	Approved
0.7281	Intermediate Similarity	NPD6314	Approved
0.7281	Intermediate Similarity	NPD6313	Approved
0.7273	Intermediate Similarity	NPD5247	Approved
0.7273	Intermediate Similarity	NPD5249	Phase 3
0.7273	Intermediate Similarity	NPD5135	Approved
0.7273	Intermediate Similarity	NPD5169	Approved
0.7273	Intermediate Similarity	NPD5251	Approved
0.7273	Intermediate Similarity	NPD5250	Approved
0.7273	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5248	Approved
0.7257	Intermediate Similarity	NPD6274	Approved
0.7253	Intermediate Similarity	NPD4058	Approved
0.7248	Intermediate Similarity	NPD5128	Approved
0.7245	Intermediate Similarity	NPD5280	Approved
0.7245	Intermediate Similarity	NPD4694	Approved
0.7245	Intermediate Similarity	NPD5690	Phase 2
0.7228	Intermediate Similarity	NPD6411	Approved
0.7228	Intermediate Similarity	NPD5694	Approved
0.7228	Intermediate Similarity	NPD6050	Approved
0.7222	Intermediate Similarity	NPD4768	Approved
0.7222	Intermediate Similarity	NPD4767	Approved
0.7216	Intermediate Similarity	NPD4197	Approved
0.7207	Intermediate Similarity	NPD5217	Approved
0.7207	Intermediate Similarity	NPD5216	Approved
0.7207	Intermediate Similarity	NPD5215	Approved
0.7207	Intermediate Similarity	NPD5127	Approved
0.7204	Intermediate Similarity	NPD6116	Phase 1
0.72	Intermediate Similarity	NPD6904	Approved
0.72	Intermediate Similarity	NPD6080	Approved
0.72	Intermediate Similarity	NPD6673	Approved
0.7158	Intermediate Similarity	NPD4252	Approved
0.7158	Intermediate Similarity	NPD4695	Discontinued
0.7158	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD1696	Phase 3
0.7129	Intermediate Similarity	NPD5207	Approved
0.7129	Intermediate Similarity	NPD5692	Phase 3
0.7128	Intermediate Similarity	NPD6114	Approved
0.7128	Intermediate Similarity	NPD6118	Approved
0.7128	Intermediate Similarity	NPD6115	Approved
0.7128	Intermediate Similarity	NPD3617	Approved
0.7128	Intermediate Similarity	NPD6697	Approved
0.7119	Intermediate Similarity	NPD7604	Phase 2
0.7094	Intermediate Similarity	NPD5983	Phase 2
0.7094	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6686	Approved
0.7071	Intermediate Similarity	NPD4688	Approved
0.7071	Intermediate Similarity	NPD4693	Phase 3
0.7071	Intermediate Similarity	NPD4690	Approved
0.7071	Intermediate Similarity	NPD4689	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.7071	Intermediate Similarity	NPD5205	Approved
0.7071	Intermediate Similarity	NPD4138	Approved
0.7065	Intermediate Similarity	NPD6926	Approved
0.7065	Intermediate Similarity	NPD6924	Approved
0.7065	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD7492	Approved
0.7053	Intermediate Similarity	NPD6929	Approved
0.7053	Intermediate Similarity	NPD4195	Approved
0.7033	Intermediate Similarity	NPD7151	Approved
0.7033	Intermediate Similarity	NPD7152	Approved
0.7033	Intermediate Similarity	NPD7150	Approved
0.703	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5167	Approved
0.7009	Intermediate Similarity	NPD6054	Approved
0.7	Intermediate Similarity	NPD6412	Phase 2
0.7	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD6336	Discontinued
0.6989	Remote Similarity	NPD6942	Approved
0.6989	Remote Similarity	NPD7339	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