NPASS Compound

Structure

NPC57079 OpenBabel07101718282D 35 37 0 0 1 0 0 0 0 0999 V2000 -0.2308 -3.6974 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 0.4894 -7.0858 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 3.7840 -8.1563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 -1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1074 -5.1837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 -2.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4164 -4.2327 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 1.7766 -5.9269 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 0.7473 -3.4895 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 1.4675 -6.8779 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 2.1367 -7.6211 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 1.8277 -8.5721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1148 -7.4131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 8 35 1 0 0 0 0 9 11 1 0 0 0 0 9 13 2 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 2 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 31 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 32 2 0 0 0 0 24 29 1 0 0 0 0 24 30 1 6 0 0 0 25 30 1 1 0 0 0 25 31 1 0 0 0 0 26 29 1 0 0 0 0 26 33 1 6 0 0 0 27 31 1 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 30 6 1 6 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.32
Volume:	535.768
LogP:	4.791
LogD:	4.493
LogS:	-5.332
# Rotatable Bonds:	6
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	4.701
Fsp3:	0.613
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:	-5.01
MDCK Permeability:	2.501445123925805e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.349
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	94.8772964477539%
Volume Distribution (VD):	1.412
Pgp-substrate:	5.743520259857178%

ADMET: Metabolism

CYP1A2-inhibitor:	0.319
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.786
CYP2C19-substrate:	0.909
CYP2C9-inhibitor:	0.892
CYP2C9-substrate:	0.712
CYP2D6-inhibitor:	0.925
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.76

ADMET: Excretion

Clearance (CL):	6.702
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.332
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.805
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.941
Carcinogencity:	0.195
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC57079

Natural Product ID:	NPC57079
*Common Name:**	Rhabdastrellin E
IUPAC Name:	methyl (2E,4E,6E,8E,10E)-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-tetraenoate
Synonyms:	Rhabdastrellin E
Standard InCHIKey:	YEBUSFMLGJIWGK-PVOUNATJSA-N
Standard InCHI:	InChI=1S/C31H44O4/c1-20(12-10-14-22(3)28(34)35-8)11-9-13-21(2)27-23(32)19-25-30(6)18-16-26(33)29(4,5)24(30)15-17-31(25,27)7/h9-14,24-26,33H,15-19H2,1-8H3/b12-10+,13-9+,20-11+,22-14+,27-21-/t24-,25-,26-,30-,31-/m0/s1
SMILES:	COC(=O)/C(=C/C=C/C(=C/C=C/C(=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)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489190
PubChem CID:	25137305
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
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620246]
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18826276]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[456105]

☑ 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 NPC57079 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	179
0.1-0.2	858
0.2-0.3	3322
0.3-0.4	7331
0.4-0.5	14096
0.5-0.6	7045
0.6-0.7	6364
0.7-0.8	3099
0.8-0.85	324
0.85-0.9	55
0.9-0.95	20
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC108368
0.9565	High Similarity	NPC250757
0.9565	High Similarity	NPC301534
0.9474	High Similarity	NPC32577
0.9474	High Similarity	NPC155332
0.9474	High Similarity	NPC114540
0.9381	High Similarity	NPC266570
0.9263	High Similarity	NPC266955
0.9255	High Similarity	NPC253826
0.9184	High Similarity	NPC189863
0.9167	High Similarity	NPC282524
0.9167	High Similarity	NPC115899
0.9149	High Similarity	NPC471153
0.914	High Similarity	NPC299100
0.9091	High Similarity	NPC329048
0.9091	High Similarity	NPC330011
0.9053	High Similarity	NPC2049
0.9053	High Similarity	NPC110937
0.9043	High Similarity	NPC180950
0.9043	High Similarity	NPC88310
0.9022	High Similarity	NPC475965
0.9022	High Similarity	NPC474842
0.898	High Similarity	NPC473283
0.898	High Similarity	NPC329345
0.898	High Similarity	NPC72151
0.898	High Similarity	NPC475526
0.8969	High Similarity	NPC168319
0.8969	High Similarity	NPC194028
0.8936	High Similarity	NPC474690
0.8925	High Similarity	NPC473986
0.8925	High Similarity	NPC474018
0.8911	High Similarity	NPC475065
0.8901	High Similarity	NPC141292
0.8878	High Similarity	NPC320447
0.8866	High Similarity	NPC201406
0.8866	High Similarity	NPC35751
0.883	High Similarity	NPC139692
0.8812	High Similarity	NPC473482
0.8812	High Similarity	NPC475418
0.8812	High Similarity	NPC318363
0.8804	High Similarity	NPC310752
0.8804	High Similarity	NPC292491
0.8788	High Similarity	NPC112009
0.8788	High Similarity	NPC475050
0.8738	High Similarity	NPC474315
0.8713	High Similarity	NPC473284
0.866	High Similarity	NPC474785
0.866	High Similarity	NPC108078
0.866	High Similarity	NPC474938
0.8646	High Similarity	NPC139459
0.8646	High Similarity	NPC209355
0.8641	High Similarity	NPC16270
0.8632	High Similarity	NPC152778
0.8632	High Similarity	NPC162615
0.8632	High Similarity	NPC205034
0.8632	High Similarity	NPC472871
0.8617	High Similarity	NPC310479
0.8602	High Similarity	NPC104560
0.86	High Similarity	NPC476237
0.86	High Similarity	NPC180204
0.8586	High Similarity	NPC476223
0.8586	High Similarity	NPC476240
0.8586	High Similarity	NPC118174
0.8586	High Similarity	NPC471412
0.8586	High Similarity	NPC224720
0.8571	High Similarity	NPC316598
0.8571	High Similarity	NPC73050
0.8571	High Similarity	NPC98868
0.8571	High Similarity	NPC103051
0.8557	High Similarity	NPC16967
0.8557	High Similarity	NPC106425
0.8557	High Similarity	NPC242848
0.8557	High Similarity	NPC190713
0.8557	High Similarity	NPC122324
0.8557	High Similarity	NPC234993
0.8557	High Similarity	NPC151725
0.8557	High Similarity	NPC134072
0.8542	High Similarity	NPC473431
0.8542	High Similarity	NPC469406
0.8542	High Similarity	NPC471078
0.8542	High Similarity	NPC473280
0.8542	High Similarity	NPC473435
0.8542	High Similarity	NPC191521
0.8529	High Similarity	NPC475294
0.8515	High Similarity	NPC472868
0.8511	High Similarity	NPC5509
0.8511	High Similarity	NPC174342
0.8485	Intermediate Similarity	NPC476274
0.8485	Intermediate Similarity	NPC476303
0.8485	Intermediate Similarity	NPC117685
0.8485	Intermediate Similarity	NPC471413
0.8485	Intermediate Similarity	NPC251680
0.8469	Intermediate Similarity	NPC202705
0.8469	Intermediate Similarity	NPC474343
0.8462	Intermediate Similarity	NPC474790
0.8462	Intermediate Similarity	NPC474976
0.8462	Intermediate Similarity	NPC179642
0.8454	Intermediate Similarity	NPC476174
0.8454	Intermediate Similarity	NPC183012
0.8454	Intermediate Similarity	NPC293052
0.8454	Intermediate Similarity	NPC171395
0.8447	Intermediate Similarity	NPC220155
0.8438	Intermediate Similarity	NPC214697
0.8431	Intermediate Similarity	NPC34768
0.8426	Intermediate Similarity	NPC146786
0.8421	Intermediate Similarity	NPC477147
0.8421	Intermediate Similarity	NPC182136
0.8421	Intermediate Similarity	NPC477149
0.8421	Intermediate Similarity	NPC51486
0.8421	Intermediate Similarity	NPC161638
0.8416	Intermediate Similarity	NPC171014
0.8416	Intermediate Similarity	NPC176883
0.8396	Intermediate Similarity	NPC122056
0.8384	Intermediate Similarity	NPC252295
0.8384	Intermediate Similarity	NPC478056
0.8384	Intermediate Similarity	NPC114274
0.8384	Intermediate Similarity	NPC92275
0.8384	Intermediate Similarity	NPC235464
0.8384	Intermediate Similarity	NPC166745
0.8367	Intermediate Similarity	NPC472941
0.8367	Intermediate Similarity	NPC456
0.8367	Intermediate Similarity	NPC78473
0.8367	Intermediate Similarity	NPC473153
0.8351	Intermediate Similarity	NPC8993
0.8351	Intermediate Similarity	NPC91010
0.8351	Intermediate Similarity	NPC49670
0.8351	Intermediate Similarity	NPC477129
0.8351	Intermediate Similarity	NPC477130
0.8351	Intermediate Similarity	NPC38830
0.835	Intermediate Similarity	NPC179380
0.8333	Intermediate Similarity	NPC272746
0.8333	Intermediate Similarity	NPC472975
0.8333	Intermediate Similarity	NPC72845
0.8333	Intermediate Similarity	NPC212948
0.8333	Intermediate Similarity	NPC473998
0.8333	Intermediate Similarity	NPC475806
0.8318	Intermediate Similarity	NPC67259
0.8318	Intermediate Similarity	NPC147912
0.8317	Intermediate Similarity	NPC293753
0.8317	Intermediate Similarity	NPC476081
0.8317	Intermediate Similarity	NPC162973
0.8317	Intermediate Similarity	NPC136289
0.8316	Intermediate Similarity	NPC84271
0.8316	Intermediate Similarity	NPC102414
0.8316	Intermediate Similarity	NPC66344
0.8316	Intermediate Similarity	NPC475921
0.8316	Intermediate Similarity	NPC262858
0.8316	Intermediate Similarity	NPC128496
0.8316	Intermediate Similarity	NPC474704
0.8316	Intermediate Similarity	NPC36668
0.8316	Intermediate Similarity	NPC118011
0.8316	Intermediate Similarity	NPC214387
0.8316	Intermediate Similarity	NPC77168
0.8316	Intermediate Similarity	NPC309603
0.8316	Intermediate Similarity	NPC472240
0.8316	Intermediate Similarity	NPC473999
0.8316	Intermediate Similarity	NPC474844
0.8302	Intermediate Similarity	NPC264634
0.8302	Intermediate Similarity	NPC475970
0.8302	Intermediate Similarity	NPC69291
0.83	Intermediate Similarity	NPC470074
0.83	Intermediate Similarity	NPC476299
0.83	Intermediate Similarity	NPC474012
0.8298	Intermediate Similarity	NPC474684
0.8298	Intermediate Similarity	NPC142361
0.8283	Intermediate Similarity	NPC141401
0.8283	Intermediate Similarity	NPC208094
0.8283	Intermediate Similarity	NPC320306
0.8283	Intermediate Similarity	NPC99726
0.828	Intermediate Similarity	NPC106416
0.828	Intermediate Similarity	NPC86316
0.828	Intermediate Similarity	NPC470574
0.828	Intermediate Similarity	NPC109528
0.828	Intermediate Similarity	NPC65661
0.8273	Intermediate Similarity	NPC476962
0.8269	Intermediate Similarity	NPC472825
0.8265	Intermediate Similarity	NPC470016
0.8265	Intermediate Similarity	NPC317586
0.8265	Intermediate Similarity	NPC295347
0.8265	Intermediate Similarity	NPC33473
0.8261	Intermediate Similarity	NPC3856
0.8261	Intermediate Similarity	NPC279639
0.8257	Intermediate Similarity	NPC473828
0.8257	Intermediate Similarity	NPC473617
0.8252	Intermediate Similarity	NPC295843
0.8247	Intermediate Similarity	NPC141497
0.8247	Intermediate Similarity	NPC38232
0.8247	Intermediate Similarity	NPC107674
0.8247	Intermediate Similarity	NPC214756
0.8247	Intermediate Similarity	NPC295643
0.8247	Intermediate Similarity	NPC272075
0.8247	Intermediate Similarity	NPC476304
0.8247	Intermediate Similarity	NPC170220
0.8242	Intermediate Similarity	NPC40228
0.8235	Intermediate Similarity	NPC297617
0.8235	Intermediate Similarity	NPC120321
0.8235	Intermediate Similarity	NPC476889
0.8229	Intermediate Similarity	NPC221111
0.8229	Intermediate Similarity	NPC126993
0.8229	Intermediate Similarity	NPC280149

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 NPC57079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1052
0.2-0.3	3240
0.3-0.4	2904
0.4-0.5	1192
0.5-0.6	256
0.6-0.7	190
0.7-0.8	149
0.8-0.85	18
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7638	Approved
0.8485	Intermediate Similarity	NPD7640	Approved
0.8485	Intermediate Similarity	NPD7639	Approved
0.8333	Intermediate Similarity	NPD6079	Approved
0.8191	Intermediate Similarity	NPD3618	Phase 1
0.8165	Intermediate Similarity	NPD7115	Discovery
0.8144	Intermediate Similarity	NPD7515	Phase 2
0.8125	Intermediate Similarity	NPD5328	Approved
0.8095	Intermediate Similarity	NPD6899	Approved
0.8095	Intermediate Similarity	NPD6881	Approved
0.8	Intermediate Similarity	NPD5222	Approved
0.8	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5697	Approved
0.8	Intermediate Similarity	NPD5221	Approved
0.798	Intermediate Similarity	NPD7748	Approved
0.7957	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7290	Approved
0.7944	Intermediate Similarity	NPD7102	Approved
0.7944	Intermediate Similarity	NPD6883	Approved
0.7925	Intermediate Similarity	NPD6011	Approved
0.7921	Intermediate Similarity	NPD5173	Approved
0.7905	Intermediate Similarity	NPD5739	Approved
0.7905	Intermediate Similarity	NPD6675	Approved
0.7905	Intermediate Similarity	NPD6402	Approved
0.7905	Intermediate Similarity	NPD7128	Approved
0.7895	Intermediate Similarity	NPD1694	Approved
0.7879	Intermediate Similarity	NPD6399	Phase 3
0.787	Intermediate Similarity	NPD6650	Approved
0.787	Intermediate Similarity	NPD6617	Approved
0.787	Intermediate Similarity	NPD6649	Approved
0.787	Intermediate Similarity	NPD6869	Approved
0.787	Intermediate Similarity	NPD8130	Phase 1
0.787	Intermediate Similarity	NPD6847	Approved
0.7857	Intermediate Similarity	NPD5785	Approved
0.785	Intermediate Similarity	NPD6013	Approved
0.785	Intermediate Similarity	NPD6012	Approved
0.785	Intermediate Similarity	NPD6014	Approved
0.7843	Intermediate Similarity	NPD4225	Approved
0.7812	Intermediate Similarity	NPD6409	Approved
0.7812	Intermediate Similarity	NPD7146	Approved
0.7812	Intermediate Similarity	NPD5330	Approved
0.7812	Intermediate Similarity	NPD7334	Approved
0.7812	Intermediate Similarity	NPD7521	Approved
0.7812	Intermediate Similarity	NPD6684	Approved
0.7798	Intermediate Similarity	NPD8297	Approved
0.7798	Intermediate Similarity	NPD6882	Approved
0.7789	Intermediate Similarity	NPD3666	Approved
0.7789	Intermediate Similarity	NPD4786	Approved
0.7789	Intermediate Similarity	NPD3133	Approved
0.7789	Intermediate Similarity	NPD3665	Phase 1
0.7788	Intermediate Similarity	NPD7632	Discontinued
0.7788	Intermediate Similarity	NPD5211	Phase 2
0.7767	Intermediate Similarity	NPD5286	Approved
0.7767	Intermediate Similarity	NPD4696	Approved
0.7767	Intermediate Similarity	NPD5285	Approved
0.7766	Intermediate Similarity	NPD3667	Approved
0.7757	Intermediate Similarity	NPD7320	Approved
0.7745	Intermediate Similarity	NPD6084	Phase 2
0.7745	Intermediate Similarity	NPD6083	Phase 2
0.7745	Intermediate Similarity	NPD7902	Approved
0.7708	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD4202	Approved
0.7692	Intermediate Similarity	NPD5223	Approved
0.7685	Intermediate Similarity	NPD6373	Approved
0.7685	Intermediate Similarity	NPD6372	Approved
0.7664	Intermediate Similarity	NPD5701	Approved
0.7653	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD5737	Approved
0.7653	Intermediate Similarity	NPD6672	Approved
0.7653	Intermediate Similarity	NPD6903	Approved
0.7647	Intermediate Similarity	NPD4697	Phase 3
0.7642	Intermediate Similarity	NPD5141	Approved
0.7629	Intermediate Similarity	NPD5279	Phase 3
0.7619	Intermediate Similarity	NPD5224	Approved
0.7619	Intermediate Similarity	NPD4633	Approved
0.7619	Intermediate Similarity	NPD5226	Approved
0.7619	Intermediate Similarity	NPD5225	Approved
0.76	Intermediate Similarity	NPD5281	Approved
0.76	Intermediate Similarity	NPD5284	Approved
0.7589	Intermediate Similarity	NPD6868	Approved
0.7573	Intermediate Similarity	NPD4755	Approved
0.7568	Intermediate Similarity	NPD4632	Approved
0.7547	Intermediate Similarity	NPD5174	Approved
0.7547	Intermediate Similarity	NPD5175	Approved
0.7545	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6335	Approved
0.7451	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7900	Approved
0.7449	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6686	Approved
0.7429	Intermediate Similarity	NPD4700	Approved
0.7426	Intermediate Similarity	NPD5693	Phase 1
0.7426	Intermediate Similarity	NPD8035	Phase 2
0.7426	Intermediate Similarity	NPD7637	Suspended
0.7426	Intermediate Similarity	NPD8034	Phase 2
0.74	Intermediate Similarity	NPD4753	Phase 2
0.7391	Intermediate Similarity	NPD7101	Approved
0.7391	Intermediate Similarity	NPD7100	Approved
0.7379	Intermediate Similarity	NPD5210	Approved
0.7379	Intermediate Similarity	NPD4629	Approved
0.7379	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5695	Phase 3
0.7374	Intermediate Similarity	NPD3573	Approved
0.7368	Intermediate Similarity	NPD6317	Approved
0.7368	Intermediate Similarity	NPD6009	Approved
0.7347	Intermediate Similarity	NPD5363	Approved
0.7333	Intermediate Similarity	NPD5696	Approved
0.7304	Intermediate Similarity	NPD6313	Approved
0.7304	Intermediate Similarity	NPD6314	Approved
0.7281	Intermediate Similarity	NPD6274	Approved
0.7273	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD5168	Approved
0.7273	Intermediate Similarity	NPD4730	Approved
0.7255	Intermediate Similarity	NPD6050	Approved
0.7255	Intermediate Similarity	NPD5694	Approved
0.7255	Intermediate Similarity	NPD6411	Approved
0.7245	Intermediate Similarity	NPD3668	Phase 3
0.7228	Intermediate Similarity	NPD6904	Approved
0.7228	Intermediate Similarity	NPD6673	Approved
0.7228	Intermediate Similarity	NPD6080	Approved
0.7228	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4754	Approved
0.7216	Intermediate Similarity	NPD4223	Phase 3
0.7216	Intermediate Similarity	NPD4221	Approved
0.7207	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7525	Registered
0.7184	Intermediate Similarity	NPD5779	Approved
0.7184	Intermediate Similarity	NPD5778	Approved
0.7179	Intermediate Similarity	NPD6319	Approved
0.7172	Intermediate Similarity	NPD5329	Approved
0.7167	Intermediate Similarity	NPD7507	Approved
0.7157	Intermediate Similarity	NPD5692	Phase 3
0.7157	Intermediate Similarity	NPD5207	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD5250	Approved
0.7128	Intermediate Similarity	NPD6117	Approved
0.7119	Intermediate Similarity	NPD7503	Approved
0.7119	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5983	Phase 2
0.7117	Intermediate Similarity	NPD5128	Approved
0.7103	Intermediate Similarity	NPD6404	Discontinued
0.71	Intermediate Similarity	NPD4694	Approved
0.71	Intermediate Similarity	NPD5690	Phase 2
0.71	Intermediate Similarity	NPD4623	Approved
0.71	Intermediate Similarity	NPD4519	Discontinued
0.71	Intermediate Similarity	NPD5280	Approved
0.7097	Intermediate Similarity	NPD4058	Approved
0.7091	Intermediate Similarity	NPD6008	Approved
0.7091	Intermediate Similarity	NPD4767	Approved
0.7091	Intermediate Similarity	NPD4768	Approved
0.7083	Intermediate Similarity	NPD7492	Approved
0.708	Intermediate Similarity	NPD5127	Approved
0.708	Intermediate Similarity	NPD5215	Approved
0.708	Intermediate Similarity	NPD5216	Approved
0.708	Intermediate Similarity	NPD5217	Approved
0.7071	Intermediate Similarity	NPD4197	Approved
0.7059	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6051	Approved
0.7059	Intermediate Similarity	NPD6101	Approved
0.7053	Intermediate Similarity	NPD6116	Phase 1
0.7048	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5209	Approved
0.7041	Intermediate Similarity	NPD4269	Approved
0.7041	Intermediate Similarity	NPD4270	Approved
0.7034	Intermediate Similarity	NPD6054	Approved
0.7027	Intermediate Similarity	NPD6412	Phase 2
0.7025	Intermediate Similarity	NPD6336	Discontinued
0.7025	Intermediate Similarity	NPD6616	Approved
0.7021	Intermediate Similarity	NPD8039	Approved
0.701	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4695	Discontinued
0.6992	Remote Similarity	NPD7319	Approved
0.6991	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6114	Approved
0.6979	Remote Similarity	NPD6115	Approved
0.6979	Remote Similarity	NPD6697	Approved
0.6979	Remote Similarity	NPD6118	Approved
0.6979	Remote Similarity	NPD3617	Approved
0.6975	Remote Similarity	NPD6909	Approved
0.6975	Remote Similarity	NPD6908	Approved
0.6967	Remote Similarity	NPD7078	Approved
0.6961	Remote Similarity	NPD5208	Approved
0.6952	Remote Similarity	NPD6001	Approved
0.6939	Remote Similarity	NPD5369	Approved
0.6931	Remote Similarity	NPD4138	Approved
0.6931	Remote Similarity	NPD4693	Phase 3
0.6931	Remote Similarity	NPD6098	Approved
0.6931	Remote Similarity	NPD5205	Approved
0.6931	Remote Similarity	NPD4689	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