NPASS Compound

Structure

NPC266955 OpenBabel07101718222D 36 38 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 -2.5981 4.5000 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 2.5472 -2.4190 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 6.0997 -4.9449 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 -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 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8126 -3.7859 0.0000 C 0 0 1 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 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4817 -3.0428 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 5 23 1 0 0 0 0 6 30 1 0 0 0 0 7 30 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 11 21 2 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 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 18 1 0 0 0 0 16 28 1 0 0 0 0 17 32 1 0 0 0 0 18 31 1 0 0 0 0 19 25 1 0 0 0 0 19 27 1 0 0 0 0 21 24 1 0 0 0 0 22 29 2 0 0 0 0 23 33 2 0 0 0 0 23 36 1 0 0 0 0 24 34 1 1 0 0 0 25 29 1 0 0 0 0 25 35 2 0 0 0 0 26 30 1 0 0 0 0 26 31 1 1 0 0 0 27 31 1 6 0 0 0 27 32 1 0 0 0 0 28 30 1 0 0 0 0 28 36 1 1 0 0 0 29 32 1 0 0 0 0 31 8 1 1 0 0 0 32 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.36
Volume:	555.701
LogP:	6.244
LogD:	4.849
LogS:	-5.644
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.182
Synthetic Accessibility Score:	4.816
Fsp3:	0.688
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:	-4.718
MDCK Permeability:	2.3929909730213694e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.8
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.593
30% Bioavailability (F30%):	0.555

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416
Plasma Protein Binding (PPB):	93.37010955810547%
Volume Distribution (VD):	1.801
Pgp-substrate:	5.221670150756836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.396
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.729
CYP3A4-substrate:	0.578

ADMET: Excretion

Clearance (CL):	5.048
Half-life (T1/2):	0.037

ADMET: Toxicity

hERG Blockers:	0.768
Human Hepatotoxicity (H-HT):	0.816
Drug-inuced Liver Injury (DILI):	0.249
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.628
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.942
Carcinogencity:	0.229
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC266955

Natural Product ID:	NPC266955
*Common Name:**	Stelliferin A
IUPAC Name:	[(3Z,3aS,5aR,7S,9aR,9bS)-3-[(3E,5E,7S)-7-hydroxy-6,10-dimethylundeca-3,5,9-trien-2-ylidene]-3a,6,6,9a-tetramethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-7-yl] acetate
Synonyms:
Standard InCHIKey:	JQQLGYJOHJVUFP-SOBFQGAKSA-N
Standard InCHI:	InChI=1S/C32H48O4/c1-20(2)13-14-24(34)21(3)11-10-12-22(4)29-25(35)19-27-31(8)18-16-28(36-23(5)33)30(6,7)26(31)15-17-32(27,29)9/h10-13,24,26-28,34H,14-19H2,1-9H3/b12-10+,21-11+,29-22+/t24-,26-,27-,28-,31-,32-/m0/s1
SMILES:	CC(=CC[C@@H](/C(=C/C=C/C(=C/1C(=O)C[C@H]2[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@]12C)OC(=O)C)/C)/C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481847
PubChem CID:	10074564
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	=	21.0	nM	PMID[544625]
NPT27	Others	Unspecified		GI50	=	34.0	nM	PMID[544625]

☑ 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 NPC266955 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	178
0.1-0.2	860
0.2-0.3	3244
0.3-0.4	7237
0.4-0.5	14109
0.5-0.6	7050
0.6-0.7	6388
0.7-0.8	3227
0.8-0.85	332
0.85-0.9	47
0.9-0.95	20
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC115899
0.9579	High Similarity	NPC32577
0.9579	High Similarity	NPC155332
0.9579	High Similarity	NPC114540
0.9462	High Similarity	NPC250757
0.9462	High Similarity	NPC301534
0.9388	High Similarity	NPC473284
0.9278	High Similarity	NPC72151
0.9263	High Similarity	NPC108368
0.9263	High Similarity	NPC57079
0.9247	High Similarity	NPC474690
0.9175	High Similarity	NPC320447
0.9158	High Similarity	NPC110937
0.9082	High Similarity	NPC475526
0.9082	High Similarity	NPC475050
0.9082	High Similarity	NPC473283
0.9082	High Similarity	NPC329345
0.9072	High Similarity	NPC282524
0.9053	High Similarity	NPC471153
0.9043	High Similarity	NPC299100
0.9032	High Similarity	NPC474018
0.9032	High Similarity	NPC473986
0.901	High Similarity	NPC475065
0.8958	High Similarity	NPC474938
0.8958	High Similarity	NPC474785
0.8947	High Similarity	NPC88310
0.8947	High Similarity	NPC180950
0.8925	High Similarity	NPC475965
0.8925	High Similarity	NPC474842
0.8911	High Similarity	NPC473482
0.8911	High Similarity	NPC318363
0.8911	High Similarity	NPC475418
0.89	High Similarity	NPC266570
0.8842	High Similarity	NPC471078
0.8842	High Similarity	NPC473280
0.8842	High Similarity	NPC473431
0.8842	High Similarity	NPC473435
0.8812	High Similarity	NPC329048
0.8812	High Similarity	NPC330011
0.8804	High Similarity	NPC141292
0.8776	High Similarity	NPC35751
0.8763	High Similarity	NPC141401
0.8763	High Similarity	NPC253826
0.871	High Similarity	NPC310752
0.871	High Similarity	NPC292491
0.8687	High Similarity	NPC99411
0.8687	High Similarity	NPC476223
0.8687	High Similarity	NPC194028
0.8687	High Similarity	NPC476240
0.8687	High Similarity	NPC224720
0.8687	High Similarity	NPC118174
0.8687	High Similarity	NPC168319
0.8673	High Similarity	NPC478056
0.8654	High Similarity	NPC474315
0.8646	High Similarity	NPC469406
0.8641	High Similarity	NPC10064
0.8641	High Similarity	NPC170221
0.8617	High Similarity	NPC36668
0.8617	High Similarity	NPC118011
0.86	High Similarity	NPC136289
0.8586	High Similarity	NPC476274
0.8571	High Similarity	NPC320306
0.8571	High Similarity	NPC2049
0.8571	High Similarity	NPC108078
0.8558	High Similarity	NPC6206
0.8542	High Similarity	NPC38232
0.8529	High Similarity	NPC189863
0.8526	High Similarity	NPC48010
0.8526	High Similarity	NPC477149
0.8526	High Similarity	NPC477147
0.8526	High Similarity	NPC471896
0.8515	High Similarity	NPC476237
0.8511	High Similarity	NPC104560
0.85	High Similarity	NPC115862
0.85	High Similarity	NPC81530
0.8485	Intermediate Similarity	NPC235464
0.8485	Intermediate Similarity	NPC471717
0.8485	Intermediate Similarity	NPC103051
0.8485	Intermediate Similarity	NPC316598
0.8485	Intermediate Similarity	NPC166745
0.8469	Intermediate Similarity	NPC328371
0.8469	Intermediate Similarity	NPC151725
0.8469	Intermediate Similarity	NPC122324
0.8469	Intermediate Similarity	NPC7124
0.8469	Intermediate Similarity	NPC106425
0.8454	Intermediate Similarity	NPC8993
0.8447	Intermediate Similarity	NPC475294
0.8438	Intermediate Similarity	NPC473998
0.8438	Intermediate Similarity	NPC26888
0.8438	Intermediate Similarity	NPC475806
0.8438	Intermediate Similarity	NPC470113
0.8421	Intermediate Similarity	NPC214387
0.8421	Intermediate Similarity	NPC309603
0.8421	Intermediate Similarity	NPC473999
0.8421	Intermediate Similarity	NPC128496
0.8404	Intermediate Similarity	NPC128644
0.84	Intermediate Similarity	NPC201406
0.84	Intermediate Similarity	NPC477521
0.84	Intermediate Similarity	NPC251680
0.84	Intermediate Similarity	NPC327431
0.8396	Intermediate Similarity	NPC475970
0.8384	Intermediate Similarity	NPC99726
0.8384	Intermediate Similarity	NPC474343
0.8384	Intermediate Similarity	NPC208094
0.8381	Intermediate Similarity	NPC16270
0.8367	Intermediate Similarity	NPC134067
0.8367	Intermediate Similarity	NPC469995
0.8367	Intermediate Similarity	NPC470016
0.8367	Intermediate Similarity	NPC476174
0.8367	Intermediate Similarity	NPC279974
0.8367	Intermediate Similarity	NPC174948
0.8367	Intermediate Similarity	NPC293052
0.8367	Intermediate Similarity	NPC84383
0.8367	Intermediate Similarity	NPC139459
0.8367	Intermediate Similarity	NPC317586
0.8367	Intermediate Similarity	NPC318282
0.8367	Intermediate Similarity	NPC209355
0.8367	Intermediate Similarity	NPC173875
0.8365	Intermediate Similarity	NPC472219
0.8365	Intermediate Similarity	NPC472218
0.8365	Intermediate Similarity	NPC220155
0.8365	Intermediate Similarity	NPC472217
0.8351	Intermediate Similarity	NPC152778
0.8351	Intermediate Similarity	NPC214697
0.8351	Intermediate Similarity	NPC162615
0.8351	Intermediate Similarity	NPC205034
0.8351	Intermediate Similarity	NPC139692
0.8349	Intermediate Similarity	NPC473617
0.8349	Intermediate Similarity	NPC473828
0.8333	Intermediate Similarity	NPC175628
0.8333	Intermediate Similarity	NPC78973
0.8333	Intermediate Similarity	NPC111585
0.8333	Intermediate Similarity	NPC112009
0.8333	Intermediate Similarity	NPC95899
0.8333	Intermediate Similarity	NPC232202
0.8333	Intermediate Similarity	NPC310479
0.8333	Intermediate Similarity	NPC148414
0.8333	Intermediate Similarity	NPC222153
0.8333	Intermediate Similarity	NPC182136
0.8333	Intermediate Similarity	NPC180204
0.8318	Intermediate Similarity	NPC122056
0.8317	Intermediate Similarity	NPC303559
0.8316	Intermediate Similarity	NPC472220
0.8316	Intermediate Similarity	NPC473879
0.8316	Intermediate Similarity	NPC97884
0.83	Intermediate Similarity	NPC114274
0.83	Intermediate Similarity	NPC477813
0.83	Intermediate Similarity	NPC48647
0.83	Intermediate Similarity	NPC98868
0.8298	Intermediate Similarity	NPC322159
0.8298	Intermediate Similarity	NPC473226
0.8298	Intermediate Similarity	NPC325594
0.8298	Intermediate Similarity	NPC82979
0.8283	Intermediate Similarity	NPC234993
0.8283	Intermediate Similarity	NPC249954
0.8283	Intermediate Similarity	NPC16967
0.8283	Intermediate Similarity	NPC473153
0.8283	Intermediate Similarity	NPC472941
0.8283	Intermediate Similarity	NPC456
0.8283	Intermediate Similarity	NPC242848
0.8283	Intermediate Similarity	NPC134072
0.8265	Intermediate Similarity	NPC159410
0.8265	Intermediate Similarity	NPC74751
0.8265	Intermediate Similarity	NPC49670
0.8265	Intermediate Similarity	NPC166906
0.8265	Intermediate Similarity	NPC184870
0.8265	Intermediate Similarity	NPC38830
0.8265	Intermediate Similarity	NPC476186
0.8257	Intermediate Similarity	NPC471854
0.8252	Intermediate Similarity	NPC118911
0.8252	Intermediate Similarity	NPC472868
0.8247	Intermediate Similarity	NPC212948
0.8241	Intermediate Similarity	NPC475163
0.8241	Intermediate Similarity	NPC147912
0.8241	Intermediate Similarity	NPC67259
0.8235	Intermediate Similarity	NPC293753
0.8235	Intermediate Similarity	NPC234892
0.8235	Intermediate Similarity	NPC308726
0.8235	Intermediate Similarity	NPC119601
0.8235	Intermediate Similarity	NPC281702
0.8235	Intermediate Similarity	NPC473163
0.8235	Intermediate Similarity	NPC476081
0.8229	Intermediate Similarity	NPC146554
0.8229	Intermediate Similarity	NPC472240
0.8229	Intermediate Similarity	NPC474704
0.8229	Intermediate Similarity	NPC31985
0.8229	Intermediate Similarity	NPC66344
0.8229	Intermediate Similarity	NPC262858
0.8229	Intermediate Similarity	NPC474889
0.8229	Intermediate Similarity	NPC84271
0.8229	Intermediate Similarity	NPC102414
0.8229	Intermediate Similarity	NPC475921
0.8229	Intermediate Similarity	NPC77168
0.8229	Intermediate Similarity	NPC1015
0.8224	Intermediate Similarity	NPC264634
0.8224	Intermediate Similarity	NPC69291
0.8218	Intermediate Similarity	NPC477720
0.8218	Intermediate Similarity	NPC476303
0.8218	Intermediate Similarity	NPC117685
0.8218	Intermediate Similarity	NPC470074

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 NPC266955 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1038
0.2-0.3	3230
0.3-0.4	2913
0.4-0.5	1173
0.5-0.6	272
0.6-0.7	195
0.7-0.8	164
0.8-0.85	17
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD7639	Approved
0.84	Intermediate Similarity	NPD7640	Approved
0.83	Intermediate Similarity	NPD7638	Approved
0.8265	Intermediate Similarity	NPD7748	Approved
0.8163	Intermediate Similarity	NPD6399	Phase 3
0.8105	Intermediate Similarity	NPD3618	Phase 1
0.8091	Intermediate Similarity	NPD7115	Discovery
0.8061	Intermediate Similarity	NPD6079	Approved
0.8061	Intermediate Similarity	NPD7515	Phase 2
0.8041	Intermediate Similarity	NPD5328	Approved
0.802	Intermediate Similarity	NPD7902	Approved
0.8019	Intermediate Similarity	NPD6881	Approved
0.8019	Intermediate Similarity	NPD6899	Approved
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.7963	Intermediate Similarity	NPD8130	Phase 1
0.7925	Intermediate Similarity	NPD5697	Approved
0.7917	Intermediate Similarity	NPD6409	Approved
0.7917	Intermediate Similarity	NPD5330	Approved
0.7917	Intermediate Similarity	NPD7146	Approved
0.7917	Intermediate Similarity	NPD6684	Approved
0.7917	Intermediate Similarity	NPD7334	Approved
0.7917	Intermediate Similarity	NPD7521	Approved
0.7895	Intermediate Similarity	NPD4786	Approved
0.789	Intermediate Similarity	NPD8297	Approved
0.7879	Intermediate Similarity	NPD7637	Suspended
0.7872	Intermediate Similarity	NPD3667	Approved
0.787	Intermediate Similarity	NPD7102	Approved
0.787	Intermediate Similarity	NPD6883	Approved
0.787	Intermediate Similarity	NPD7290	Approved
0.785	Intermediate Similarity	NPD6011	Approved
0.785	Intermediate Similarity	NPD7320	Approved
0.7843	Intermediate Similarity	NPD6083	Phase 2
0.7843	Intermediate Similarity	NPD6084	Phase 2
0.7798	Intermediate Similarity	NPD6650	Approved
0.7798	Intermediate Similarity	NPD6649	Approved
0.7798	Intermediate Similarity	NPD6847	Approved
0.7798	Intermediate Similarity	NPD6617	Approved
0.7798	Intermediate Similarity	NPD6869	Approved
0.7778	Intermediate Similarity	NPD6373	Approved
0.7778	Intermediate Similarity	NPD6372	Approved
0.7778	Intermediate Similarity	NPD6012	Approved
0.7778	Intermediate Similarity	NPD6013	Approved
0.7778	Intermediate Similarity	NPD6014	Approved
0.7767	Intermediate Similarity	NPD4225	Approved
0.7757	Intermediate Similarity	NPD5701	Approved
0.7755	Intermediate Similarity	NPD6903	Approved
0.7755	Intermediate Similarity	NPD6672	Approved
0.7755	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5737	Approved
0.7745	Intermediate Similarity	NPD5222	Approved
0.7745	Intermediate Similarity	NPD5221	Approved
0.7745	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6882	Approved
0.7723	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7900	Approved
0.7714	Intermediate Similarity	NPD5211	Phase 2
0.7714	Intermediate Similarity	NPD7632	Discontinued
0.7708	Intermediate Similarity	NPD3665	Phase 1
0.7708	Intermediate Similarity	NPD3133	Approved
0.7708	Intermediate Similarity	NPD3666	Approved
0.77	Intermediate Similarity	NPD8035	Phase 2
0.77	Intermediate Similarity	NPD8034	Phase 2
0.767	Intermediate Similarity	NPD5173	Approved
0.7636	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5779	Approved
0.7624	Intermediate Similarity	NPD5778	Approved
0.7624	Intermediate Similarity	NPD4202	Approved
0.76	Intermediate Similarity	NPD5785	Approved
0.7573	Intermediate Similarity	NPD4697	Phase 3
0.757	Intermediate Similarity	NPD5141	Approved
0.7551	Intermediate Similarity	NPD5279	Phase 3
0.7525	Intermediate Similarity	NPD5281	Approved
0.7525	Intermediate Similarity	NPD5284	Approved
0.7525	Intermediate Similarity	NPD6411	Approved
0.7524	Intermediate Similarity	NPD5286	Approved
0.7524	Intermediate Similarity	NPD4696	Approved
0.7524	Intermediate Similarity	NPD5285	Approved
0.7522	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4755	Approved
0.7476	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5695	Phase 3
0.7453	Intermediate Similarity	NPD5223	Approved
0.7449	Intermediate Similarity	NPD5363	Approved
0.7449	Intermediate Similarity	NPD1694	Approved
0.7429	Intermediate Similarity	NPD5696	Approved
0.7423	Intermediate Similarity	NPD5362	Discontinued
0.7391	Intermediate Similarity	NPD6335	Approved
0.7383	Intermediate Similarity	NPD5226	Approved
0.7383	Intermediate Similarity	NPD5225	Approved
0.7383	Intermediate Similarity	NPD5224	Approved
0.7383	Intermediate Similarity	NPD4633	Approved
0.7358	Intermediate Similarity	NPD4700	Approved
0.7353	Intermediate Similarity	NPD5694	Approved
0.7353	Intermediate Similarity	NPD6050	Approved
0.7347	Intermediate Similarity	NPD3668	Phase 3
0.7345	Intermediate Similarity	NPD4632	Approved
0.7339	Intermediate Similarity	NPD6008	Approved
0.7328	Intermediate Similarity	NPD7100	Approved
0.7328	Intermediate Similarity	NPD7101	Approved
0.7327	Intermediate Similarity	NPD4753	Phase 2
0.7327	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6101	Approved
0.7327	Intermediate Similarity	NPD6904	Approved
0.7327	Intermediate Similarity	NPD6673	Approved
0.7327	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6080	Approved
0.732	Intermediate Similarity	NPD4269	Approved
0.732	Intermediate Similarity	NPD4270	Approved
0.7315	Intermediate Similarity	NPD5174	Approved
0.7315	Intermediate Similarity	NPD5175	Approved
0.7304	Intermediate Similarity	NPD6317	Approved
0.73	Intermediate Similarity	NPD3573	Approved
0.7292	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5207	Approved
0.7255	Intermediate Similarity	NPD5692	Phase 3
0.7245	Intermediate Similarity	NPD6695	Phase 3
0.7245	Intermediate Similarity	NPD7154	Phase 3
0.7241	Intermediate Similarity	NPD6313	Approved
0.7241	Intermediate Similarity	NPD6314	Approved
0.7217	Intermediate Similarity	NPD6274	Approved
0.72	Intermediate Similarity	NPD5786	Approved
0.72	Intermediate Similarity	NPD4623	Approved
0.72	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4519	Discontinued
0.7184	Intermediate Similarity	NPD5693	Phase 1
0.7172	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4754	Approved
0.7155	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD4221	Approved
0.7129	Intermediate Similarity	NPD7750	Discontinued
0.7128	Intermediate Similarity	NPD8264	Approved
0.7119	Intermediate Similarity	NPD6319	Approved
0.7117	Intermediate Similarity	NPD6412	Phase 2
0.7113	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4252	Approved
0.7113	Intermediate Similarity	NPD7525	Registered
0.71	Intermediate Similarity	NPD5329	Approved
0.7083	Intermediate Similarity	NPD7604	Phase 2
0.7059	Intermediate Similarity	NPD6908	Approved
0.7059	Intermediate Similarity	NPD6909	Approved
0.7059	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5208	Approved
0.7059	Intermediate Similarity	NPD5983	Phase 2
0.7054	Intermediate Similarity	NPD4729	Approved
0.7054	Intermediate Similarity	NPD4730	Approved
0.7054	Intermediate Similarity	NPD6686	Approved
0.7054	Intermediate Similarity	NPD5168	Approved
0.7053	Intermediate Similarity	NPD6117	Approved
0.7048	Intermediate Similarity	NPD6001	Approved
0.7041	Intermediate Similarity	NPD5369	Approved
0.7037	Intermediate Similarity	NPD6404	Discontinued
0.703	Intermediate Similarity	NPD6098	Approved
0.703	Intermediate Similarity	NPD5280	Approved
0.703	Intermediate Similarity	NPD4694	Approved
0.7027	Intermediate Similarity	NPD4768	Approved
0.7027	Intermediate Similarity	NPD4767	Approved
0.7025	Intermediate Similarity	NPD7492	Approved
0.7021	Intermediate Similarity	NPD6924	Approved
0.7021	Intermediate Similarity	NPD6926	Approved
0.701	Intermediate Similarity	NPD6929	Approved
0.7	Intermediate Similarity	NPD4197	Approved
0.6992	Remote Similarity	NPD7736	Approved
0.6991	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7151	Approved
0.6989	Remote Similarity	NPD7150	Approved
0.6989	Remote Similarity	NPD7152	Approved
0.6979	Remote Similarity	NPD6116	Phase 1
0.6975	Remote Similarity	NPD6054	Approved
0.697	Remote Similarity	NPD6435	Approved
0.6967	Remote Similarity	NPD7507	Approved
0.6967	Remote Similarity	NPD6616	Approved
0.6967	Remote Similarity	NPD6336	Discontinued
0.6961	Remote Similarity	NPD7524	Approved
0.6947	Remote Similarity	NPD6942	Approved
0.6947	Remote Similarity	NPD7339	Approved
0.6947	Remote Similarity	NPD8039	Approved
0.6939	Remote Similarity	NPD4695	Discontinued
0.6939	Remote Similarity	NPD6930	Phase 2
0.6939	Remote Similarity	NPD7514	Phase 3
0.6939	Remote Similarity	NPD4822	Approved
0.6939	Remote Similarity	NPD6931	Approved
0.6939	Remote Similarity	NPD4821	Approved
0.6939	Remote Similarity	NPD4820	Approved
0.6939	Remote Similarity	NPD4819	Approved
0.6931	Remote Similarity	NPD1696	Phase 3
0.693	Remote Similarity	NPD5169	Approved
0.693	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5249	Phase 3
0.693	Remote Similarity	NPD5250	Approved
0.693	Remote Similarity	NPD5247	Approved
0.693	Remote Similarity	NPD4634	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