NPASS Compound

Structure

NPC26888 OpenBabel07101718312D 36 39 0 0 1 0 0 0 0 0999 V2000 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 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 2.1871 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -1.0181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 -1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 4 22 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 8 31 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 21 3 1 1 0 0 0 21 23 1 0 0 0 0 22 33 2 0 0 0 0 22 36 1 0 0 0 0 23 31 1 1 0 0 0 24 25 2 0 0 0 0 24 30 1 0 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 1 0 0 0 27 29 1 0 0 0 0 27 36 1 1 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 30 7 1 1 0 0 0 31 32 1 1 0 0 0 32 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	552.417
LogP:	7.591
LogD:	5.591
LogS:	-5.333
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	4.72
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.235
MDCK Permeability:	1.995501952478662e-05
Pgp-inhibitor:	0.176
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.589
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	92.19303131103516%
Volume Distribution (VD):	0.869
Pgp-substrate:	1.495608925819397%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.142
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.334
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.324
CYP3A4-substrate:	0.644

ADMET: Excretion

Clearance (CL):	2.688
Half-life (T1/2):	0.025

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.689
Drug-inuced Liver Injury (DILI):	0.115
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.502
Skin Sensitization:	0.16
Carcinogencity:	0.055
Eye Corrosion:	0.796
Eye Irritation:	0.234
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC26888

Natural Product ID:	NPC26888
*Common Name:**	Acetylpenasterol
IUPAC Name:	(3S,5R,10S,13R,14S,17R)-3-acetyloxy-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid
Synonyms:	Acetylpenasterol
Standard InCHIKey:	OKLAKFASQGMWRS-RDXQEYJHSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-20(2)10-9-11-21(3)23-15-19-32(28(34)35)25-12-13-26-29(5,6)27(36-22(4)33)16-17-30(26,7)24(25)14-18-31(23,32)8/h10,21,23,26-27H,9,11-19H2,1-8H3,(H,34,35)/t21-,23-,26+,27+,30-,31-,32+/m1/s1
SMILES:	CC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)OC(=O)C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477536
PubChem CID:	44584702
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
NPO33198	penares incrustans	Species	Geodiidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[1282538]

☑ 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
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	10000.0	nM	PMID[501000]
NPT27	Others	Unspecified		Activity	=	97.0	%	PMID[501000]

☑ 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 NPC26888 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	165
0.1-0.2	1014
0.2-0.3	4441
0.3-0.4	13133
0.4-0.5	9312
0.5-0.6	5879
0.6-0.7	5801
0.7-0.8	2544
0.8-0.85	296
0.85-0.9	85
0.9-0.95	22
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC148414
0.9882	High Similarity	NPC111585
0.9882	High Similarity	NPC175628
0.9765	High Similarity	NPC474889
0.9651	High Similarity	NPC471896
0.9419	High Similarity	NPC242864
0.9333	High Similarity	NPC120708
0.9302	High Similarity	NPC187376
0.9302	High Similarity	NPC159046
0.9302	High Similarity	NPC233836
0.9222	High Similarity	NPC184848
0.9222	High Similarity	NPC69548
0.9186	High Similarity	NPC28252
0.9186	High Similarity	NPC55309
0.913	High Similarity	NPC477813
0.9111	High Similarity	NPC159410
0.9101	High Similarity	NPC297265
0.9091	High Similarity	NPC474704
0.9091	High Similarity	NPC77168
0.9091	High Similarity	NPC475921
0.9091	High Similarity	NPC84271
0.9091	High Similarity	NPC102414
0.908	High Similarity	NPC474684
0.908	High Similarity	NPC142361
0.9011	High Similarity	NPC470016
0.9011	High Similarity	NPC317586
0.9011	High Similarity	NPC279974
0.9	High Similarity	NPC470224
0.8989	High Similarity	NPC469400
0.8966	High Similarity	NPC474970
0.8966	High Similarity	NPC264127
0.8966	High Similarity	NPC155011
0.8966	High Similarity	NPC325594
0.8936	High Similarity	NPC473514
0.8913	High Similarity	NPC173272
0.8913	High Similarity	NPC327788
0.8901	High Similarity	NPC166906
0.8901	High Similarity	NPC469406
0.8889	High Similarity	NPC77099
0.8889	High Similarity	NPC470590
0.8889	High Similarity	NPC23434
0.8889	High Similarity	NPC285184
0.8889	High Similarity	NPC60755
0.8889	High Similarity	NPC189520
0.8876	High Similarity	NPC474570
0.8864	High Similarity	NPC167877
0.8842	High Similarity	NPC473788
0.8842	High Similarity	NPC475558
0.8804	High Similarity	NPC45324
0.8804	High Similarity	NPC48330
0.8804	High Similarity	NPC222845
0.8804	High Similarity	NPC469599
0.8804	High Similarity	NPC473648
0.8804	High Similarity	NPC162001
0.8791	High Similarity	NPC470375
0.8791	High Similarity	NPC470376
0.8791	High Similarity	NPC141497
0.8791	High Similarity	NPC107674
0.8791	High Similarity	NPC170220
0.8778	High Similarity	NPC120840
0.8778	High Similarity	NPC113989
0.8778	High Similarity	NPC20388
0.8778	High Similarity	NPC474728
0.8764	High Similarity	NPC4309
0.8764	High Similarity	NPC97884
0.8764	High Similarity	NPC472220
0.8764	High Similarity	NPC471722
0.875	High Similarity	NPC94755
0.875	High Similarity	NPC73038
0.8723	High Similarity	NPC119036
0.8721	High Similarity	NPC260956
0.871	High Similarity	NPC96859
0.871	High Similarity	NPC42042
0.871	High Similarity	NPC305483
0.871	High Similarity	NPC328162
0.8696	High Similarity	NPC474922
0.8681	High Similarity	NPC212301
0.8681	High Similarity	NPC86266
0.8681	High Similarity	NPC110657
0.8667	High Similarity	NPC128496
0.8667	High Similarity	NPC30522
0.8621	High Similarity	NPC471037
0.8617	High Similarity	NPC320306
0.8617	High Similarity	NPC141401
0.8617	High Similarity	NPC108078
0.8605	High Similarity	NPC473420
0.8605	High Similarity	NPC38350
0.8605	High Similarity	NPC201912
0.8605	High Similarity	NPC327002
0.8602	High Similarity	NPC195715
0.8588	High Similarity	NPC327674
0.8587	High Similarity	NPC86368
0.8587	High Similarity	NPC38232
0.8571	High Similarity	NPC231530
0.8571	High Similarity	NPC475494
0.8571	High Similarity	NPC44240
0.8571	High Similarity	NPC278628
0.8556	High Similarity	NPC183546
0.8556	High Similarity	NPC294480
0.8542	High Similarity	NPC99411
0.8539	High Similarity	NPC6979
0.8539	High Similarity	NPC72133
0.8526	High Similarity	NPC477854
0.8526	High Similarity	NPC48647
0.8526	High Similarity	NPC186810
0.8523	High Similarity	NPC59453
0.8523	High Similarity	NPC221758
0.8523	High Similarity	NPC100391
0.8523	High Similarity	NPC165064
0.8511	High Similarity	NPC7124
0.8511	High Similarity	NPC328371
0.8511	High Similarity	NPC327179
0.8506	High Similarity	NPC73882
0.8506	High Similarity	NPC296367
0.8495	Intermediate Similarity	NPC74751
0.8495	Intermediate Similarity	NPC78580
0.8495	Intermediate Similarity	NPC296164
0.8495	Intermediate Similarity	NPC23621
0.8495	Intermediate Similarity	NPC184006
0.8495	Intermediate Similarity	NPC49670
0.8495	Intermediate Similarity	NPC471720
0.8478	Intermediate Similarity	NPC160506
0.8478	Intermediate Similarity	NPC154101
0.8478	Intermediate Similarity	NPC471901
0.8462	Intermediate Similarity	NPC1015
0.8462	Intermediate Similarity	NPC143232
0.8462	Intermediate Similarity	NPC31985
0.8462	Intermediate Similarity	NPC198664
0.8462	Intermediate Similarity	NPC54689
0.8462	Intermediate Similarity	NPC275740
0.8462	Intermediate Similarity	NPC470588
0.8462	Intermediate Similarity	NPC32830
0.8462	Intermediate Similarity	NPC274330
0.8462	Intermediate Similarity	NPC86319
0.8462	Intermediate Similarity	NPC474245
0.8454	Intermediate Similarity	NPC136289
0.8454	Intermediate Similarity	NPC22388
0.8444	Intermediate Similarity	NPC46912
0.8444	Intermediate Similarity	NPC475740
0.8444	Intermediate Similarity	NPC312215
0.8444	Intermediate Similarity	NPC33768
0.8444	Intermediate Similarity	NPC162107
0.8444	Intermediate Similarity	NPC96496
0.8444	Intermediate Similarity	NPC71507
0.8438	Intermediate Similarity	NPC327431
0.8438	Intermediate Similarity	NPC316964
0.8438	Intermediate Similarity	NPC476303
0.8438	Intermediate Similarity	NPC266955
0.8427	Intermediate Similarity	NPC98270
0.8421	Intermediate Similarity	NPC158347
0.8421	Intermediate Similarity	NPC43747
0.8416	Intermediate Similarity	NPC197428
0.8409	Intermediate Similarity	NPC470015
0.8409	Intermediate Similarity	NPC83569
0.8409	Intermediate Similarity	NPC470948
0.8409	Intermediate Similarity	NPC168188
0.8409	Intermediate Similarity	NPC69279
0.8404	Intermediate Similarity	NPC84383
0.8404	Intermediate Similarity	NPC174948
0.8404	Intermediate Similarity	NPC474727
0.8404	Intermediate Similarity	NPC23241
0.8404	Intermediate Similarity	NPC318282
0.8404	Intermediate Similarity	NPC173875
0.8404	Intermediate Similarity	NPC469995
0.84	Intermediate Similarity	NPC472218
0.84	Intermediate Similarity	NPC472217
0.84	Intermediate Similarity	NPC94529
0.84	Intermediate Similarity	NPC472219
0.8391	Intermediate Similarity	NPC147066
0.8387	Intermediate Similarity	NPC471902
0.8387	Intermediate Similarity	NPC287118
0.8387	Intermediate Similarity	NPC49776
0.8387	Intermediate Similarity	NPC474806
0.8387	Intermediate Similarity	NPC152897
0.8387	Intermediate Similarity	NPC63118
0.8387	Intermediate Similarity	NPC477855
0.8387	Intermediate Similarity	NPC474436
0.8387	Intermediate Similarity	NPC473690
0.8387	Intermediate Similarity	NPC133579
0.8387	Intermediate Similarity	NPC206810
0.8387	Intermediate Similarity	NPC66429
0.8372	Intermediate Similarity	NPC477371
0.8372	Intermediate Similarity	NPC153987
0.8372	Intermediate Similarity	NPC44083
0.837	Intermediate Similarity	NPC191684
0.837	Intermediate Similarity	NPC126369
0.837	Intermediate Similarity	NPC111110
0.837	Intermediate Similarity	NPC477149
0.837	Intermediate Similarity	NPC123854
0.837	Intermediate Similarity	NPC470589
0.837	Intermediate Similarity	NPC477147
0.8367	Intermediate Similarity	NPC222153
0.8367	Intermediate Similarity	NPC180204
0.8367	Intermediate Similarity	NPC36688
0.8352	Intermediate Similarity	NPC17733
0.8352	Intermediate Similarity	NPC473242
0.8352	Intermediate Similarity	NPC290690
0.8352	Intermediate Similarity	NPC143767
0.8352	Intermediate Similarity	NPC471724
0.8352	Intermediate Similarity	NPC52169

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 NPC26888 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1344
0.2-0.3	3853
0.3-0.4	2561
0.4-0.5	722
0.5-0.6	197
0.6-0.7	185
0.7-0.8	143
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD6399	Phase 3
0.8523	High Similarity	NPD4786	Approved
0.8495	Intermediate Similarity	NPD7748	Approved
0.8478	Intermediate Similarity	NPD8035	Phase 2
0.8478	Intermediate Similarity	NPD8034	Phase 2
0.8295	Intermediate Similarity	NPD3667	Approved
0.8261	Intermediate Similarity	NPD5328	Approved
0.8229	Intermediate Similarity	NPD7902	Approved
0.8222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD5695	Phase 3
0.82	Intermediate Similarity	NPD5739	Approved
0.82	Intermediate Similarity	NPD6402	Approved
0.82	Intermediate Similarity	NPD6675	Approved
0.82	Intermediate Similarity	NPD7128	Approved
0.8152	Intermediate Similarity	NPD5737	Approved
0.8152	Intermediate Similarity	NPD6672	Approved
0.8132	Intermediate Similarity	NPD7146	Approved
0.8132	Intermediate Similarity	NPD3618	Phase 1
0.8132	Intermediate Similarity	NPD5330	Approved
0.8132	Intermediate Similarity	NPD7334	Approved
0.8132	Intermediate Similarity	NPD6684	Approved
0.8132	Intermediate Similarity	NPD7521	Approved
0.8132	Intermediate Similarity	NPD6409	Approved
0.8085	Intermediate Similarity	NPD7515	Phase 2
0.8085	Intermediate Similarity	NPD6079	Approved
0.8041	Intermediate Similarity	NPD6083	Phase 2
0.8041	Intermediate Similarity	NPD6084	Phase 2
0.8039	Intermediate Similarity	NPD7320	Approved
0.8039	Intermediate Similarity	NPD6899	Approved
0.8039	Intermediate Similarity	NPD6881	Approved
0.7981	Intermediate Similarity	NPD8130	Phase 1
0.7961	Intermediate Similarity	NPD6373	Approved
0.7961	Intermediate Similarity	NPD6372	Approved
0.7959	Intermediate Similarity	NPD7638	Approved
0.7957	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD6903	Approved
0.7941	Intermediate Similarity	NPD5701	Approved
0.7941	Intermediate Similarity	NPD5697	Approved
0.7917	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7900	Approved
0.7912	Intermediate Similarity	NPD3668	Phase 3
0.7905	Intermediate Similarity	NPD8297	Approved
0.7895	Intermediate Similarity	NPD6411	Approved
0.7885	Intermediate Similarity	NPD7102	Approved
0.7885	Intermediate Similarity	NPD7290	Approved
0.7885	Intermediate Similarity	NPD6883	Approved
0.7879	Intermediate Similarity	NPD7640	Approved
0.7879	Intermediate Similarity	NPD7639	Approved
0.7864	Intermediate Similarity	NPD6011	Approved
0.7835	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4202	Approved
0.781	Intermediate Similarity	NPD6650	Approved
0.781	Intermediate Similarity	NPD6617	Approved
0.781	Intermediate Similarity	NPD6649	Approved
0.781	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6869	Approved
0.781	Intermediate Similarity	NPD6847	Approved
0.7788	Intermediate Similarity	NPD6013	Approved
0.7788	Intermediate Similarity	NPD6014	Approved
0.7788	Intermediate Similarity	NPD6012	Approved
0.7778	Intermediate Similarity	NPD5696	Approved
0.7755	Intermediate Similarity	NPD5221	Approved
0.7755	Intermediate Similarity	NPD5222	Approved
0.7755	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD4697	Phase 3
0.7742	Intermediate Similarity	NPD6098	Approved
0.7742	Intermediate Similarity	NPD5279	Phase 3
0.7736	Intermediate Similarity	NPD6882	Approved
0.7717	Intermediate Similarity	NPD3666	Approved
0.7717	Intermediate Similarity	NPD3133	Approved
0.7717	Intermediate Similarity	NPD3665	Phase 1
0.7708	Intermediate Similarity	NPD5284	Approved
0.7708	Intermediate Similarity	NPD5281	Approved
0.7708	Intermediate Similarity	NPD6050	Approved
0.7701	Intermediate Similarity	NPD6942	Approved
0.7701	Intermediate Similarity	NPD7339	Approved
0.7684	Intermediate Similarity	NPD6080	Approved
0.7684	Intermediate Similarity	NPD6673	Approved
0.7684	Intermediate Similarity	NPD6101	Approved
0.7684	Intermediate Similarity	NPD6904	Approved
0.7684	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4755	Approved
0.7677	Intermediate Similarity	NPD5173	Approved
0.767	Intermediate Similarity	NPD6008	Approved
0.7667	Intermediate Similarity	NPD7525	Registered
0.7615	Intermediate Similarity	NPD7115	Discovery
0.7614	Intermediate Similarity	NPD6117	Approved
0.7604	Intermediate Similarity	NPD5692	Phase 3
0.7528	Intermediate Similarity	NPD6116	Phase 1
0.7526	Intermediate Similarity	NPD5694	Approved
0.7525	Intermediate Similarity	NPD4696	Approved
0.7525	Intermediate Similarity	NPD5286	Approved
0.7525	Intermediate Similarity	NPD4700	Approved
0.7525	Intermediate Similarity	NPD5285	Approved
0.7523	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD4223	Phase 3
0.7451	Intermediate Similarity	NPD5223	Approved
0.7447	Intermediate Similarity	NPD5329	Approved
0.7444	Intermediate Similarity	NPD6115	Approved
0.7444	Intermediate Similarity	NPD6697	Approved
0.7444	Intermediate Similarity	NPD6118	Approved
0.7444	Intermediate Similarity	NPD6114	Approved
0.7423	Intermediate Similarity	NPD5207	Approved
0.7416	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5208	Approved
0.7387	Intermediate Similarity	NPD6335	Approved
0.7386	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5225	Approved
0.7379	Intermediate Similarity	NPD5226	Approved
0.7379	Intermediate Similarity	NPD5224	Approved
0.7379	Intermediate Similarity	NPD4633	Approved
0.7379	Intermediate Similarity	NPD5211	Phase 2
0.7374	Intermediate Similarity	NPD6001	Approved
0.7368	Intermediate Similarity	NPD5280	Approved
0.7368	Intermediate Similarity	NPD4694	Approved
0.7368	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5690	Phase 2
0.7364	Intermediate Similarity	NPD6274	Approved
0.7347	Intermediate Similarity	NPD5693	Phase 1
0.734	Intermediate Similarity	NPD4197	Approved
0.7339	Intermediate Similarity	NPD4632	Approved
0.7321	Intermediate Similarity	NPD7100	Approved
0.7321	Intermediate Similarity	NPD7101	Approved
0.732	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6051	Approved
0.7308	Intermediate Similarity	NPD4754	Approved
0.7308	Intermediate Similarity	NPD5175	Approved
0.7308	Intermediate Similarity	NPD5174	Approved
0.7297	Intermediate Similarity	NPD6317	Approved
0.7292	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD5779	Approved
0.7273	Intermediate Similarity	NPD5778	Approved
0.7253	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5141	Approved
0.7234	Intermediate Similarity	NPD5362	Discontinued
0.7232	Intermediate Similarity	NPD6314	Approved
0.7232	Intermediate Similarity	NPD6313	Approved
0.7212	Intermediate Similarity	NPD7632	Discontinued
0.7204	Intermediate Similarity	NPD4139	Approved
0.7204	Intermediate Similarity	NPD4692	Approved
0.7193	Intermediate Similarity	NPD6909	Approved
0.7193	Intermediate Similarity	NPD6908	Approved
0.7188	Intermediate Similarity	NPD4688	Approved
0.7188	Intermediate Similarity	NPD4693	Phase 3
0.7188	Intermediate Similarity	NPD4690	Approved
0.7188	Intermediate Similarity	NPD4138	Approved
0.7188	Intermediate Similarity	NPD4689	Approved
0.7188	Intermediate Similarity	NPD5205	Approved
0.7174	Intermediate Similarity	NPD7645	Phase 2
0.7172	Intermediate Similarity	NPD7637	Suspended
0.717	Intermediate Similarity	NPD4767	Approved
0.717	Intermediate Similarity	NPD4768	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.713	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5210	Approved
0.7129	Intermediate Similarity	NPD5654	Approved
0.7129	Intermediate Similarity	NPD4629	Approved
0.7128	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6319	Approved
0.7103	Intermediate Similarity	NPD6412	Phase 2
0.7097	Intermediate Similarity	NPD4748	Discontinued
0.7097	Intermediate Similarity	NPD4695	Discontinued
0.7087	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD1694	Approved
0.7069	Intermediate Similarity	NPD7604	Phase 2
0.7065	Intermediate Similarity	NPD3617	Approved
0.7053	Intermediate Similarity	NPD4788	Approved
0.7043	Intermediate Similarity	NPD5983	Phase 2
0.7043	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4729	Approved
0.7037	Intermediate Similarity	NPD4730	Approved
0.7037	Intermediate Similarity	NPD5128	Approved
0.7037	Intermediate Similarity	NPD5168	Approved
0.7034	Intermediate Similarity	NPD8293	Discontinued
0.7021	Intermediate Similarity	NPD5369	Approved
0.7019	Intermediate Similarity	NPD6404	Discontinued
0.7009	Intermediate Similarity	NPD7492	Approved
0.7	Intermediate Similarity	NPD4785	Approved
0.7	Intermediate Similarity	NPD6924	Approved
0.7	Intermediate Similarity	NPD6926	Approved
0.7	Intermediate Similarity	NPD4784	Approved
0.7	Intermediate Similarity	NPD5733	Approved
0.699	Remote Similarity	NPD5959	Approved
0.6975	Remote Similarity	NPD7736	Approved
0.6966	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4243	Approved
0.6957	Remote Similarity	NPD6054	Approved
0.6957	Remote Similarity	NPD6059	Approved
0.6949	Remote Similarity	NPD6336	Discontinued
0.6949	Remote Similarity	NPD6616	Approved
0.6947	Remote Similarity	NPD6435	Approved
0.6937	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD3702	Approved
0.6915	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5249	Phase 3
0.6909	Remote Similarity	NPD5250	Approved
0.6909	Remote Similarity	NPD5169	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