NPASS Compound

Structure

NPC474970 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 4.8564 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 2.5472 2.4190 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 -2.5981 -0.5000 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 -1.7321 -3.0000 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 1.5388 -0.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 2.1871 4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8781 3.1622 0.0000 C 0 0 2 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9000 2.9543 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -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 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2308 3.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 5 20 1 0 0 0 0 8 9 1 0 0 0 0 8 21 2 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 29 1 0 0 0 0 14 18 1 0 0 0 0 14 27 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 26 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 18 3 1 1 0 0 0 18 24 1 0 0 0 0 19 4 1 1 0 0 0 19 27 1 0 0 0 0 20 31 2 0 0 0 0 20 34 1 0 0 0 0 21 29 1 0 0 0 0 22 32 1 1 0 0 0 23 9 1 6 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 30 1 1 0 0 0 25 30 1 1 0 0 0 26 29 1 1 0 0 0 27 33 1 0 0 0 0 28 30 1 1 0 0 0 28 34 1 0 0 0 0 29 6 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	523.098
LogP:	5.562
LogD:	5.244
LogS:	-5.374
# Rotatable Bonds:	7
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	4.846
Fsp3:	0.9
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:	-4.68
MDCK Permeability:	3.643091258709319e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.55
30% Bioavailability (F30%):	0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	95.78034210205078%
Volume Distribution (VD):	1.031
Pgp-substrate:	1.5619570016860962%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.112
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.331
CYP3A4-substrate:	0.525

ADMET: Excretion

Clearance (CL):	7.358
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.671
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.169
Skin Sensitization:	0.584
Carcinogencity:	0.024
Eye Corrosion:	0.041
Eye Irritation:	0.3
Respiratory Toxicity:	0.424

Download Data

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

Natural Product: NPC474970

Natural Product ID:	NPC474970
*Common Name:**	12Beta-Acetoxyergost-5-Ene-3Beta,23-Diol
IUPAC Name:	[(3S,8R,9S,10R,12R,13R,14S,17R)-3-hydroxy-17-[(2R,5R)-4-hydroxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate
Synonyms:
Standard InCHIKey:	FWOFLAFLCPNJMF-XMZRPQIDSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-17(2)19(4)27(33)14-18(3)24-10-11-25-23-9-8-21-15-22(32)12-13-29(21,6)26(23)16-28(30(24,25)7)34-20(5)31/h8,17-19,22-28,32-33H,9-16H2,1-7H3/t18-,19-,22+,23+,24-,25+,26+,27?,28-,29+,30-/m1/s1
SMILES:	CC(C)C(C)C(CC(C)C1CCC2C1(C(CC3C2CC=C4C3(CCC(C4)O)C)OC(=O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490526
PubChem CID:	44566213
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols and derivatives

*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
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608844]
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	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
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	Activity	=	42.0	%	PMID[488228]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	3.0	mm	PMID[488228]

☑ 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 NPC474970 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	159
0.1-0.2	1077
0.2-0.3	4644
0.3-0.4	14790
0.4-0.5	7990
0.5-0.6	5506
0.6-0.7	5071
0.7-0.8	2967
0.8-0.85	386
0.85-0.9	100
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9136	High Similarity	NPC142163
0.9125	High Similarity	NPC44083
0.9125	High Similarity	NPC153987
0.907	High Similarity	NPC471896
0.8989	High Similarity	NPC276103
0.8989	High Similarity	NPC54248
0.8989	High Similarity	NPC253115
0.8989	High Similarity	NPC304899
0.8977	High Similarity	NPC474922
0.8966	High Similarity	NPC234335
0.8966	High Similarity	NPC26888
0.8953	High Similarity	NPC473647
0.8953	High Similarity	NPC475921
0.8953	High Similarity	NPC474704
0.8941	High Similarity	NPC474684
0.8941	High Similarity	NPC142361
0.8889	High Similarity	NPC100906
0.8889	High Similarity	NPC475033
0.8889	High Similarity	NPC475032
0.8864	High Similarity	NPC38232
0.8864	High Similarity	NPC470224
0.8851	High Similarity	NPC111585
0.8851	High Similarity	NPC175628
0.8851	High Similarity	NPC148414
0.8837	High Similarity	NPC242864
0.8824	High Similarity	NPC155011
0.878	High Similarity	NPC206735
0.8778	High Similarity	NPC88009
0.8765	High Similarity	NPC275910
0.875	High Similarity	NPC240604
0.875	High Similarity	NPC189883
0.875	High Similarity	NPC189520
0.875	High Similarity	NPC177641
0.875	High Similarity	NPC300324
0.875	High Similarity	NPC321016
0.875	High Similarity	NPC321381
0.875	High Similarity	NPC107059
0.8736	High Similarity	NPC472240
0.8736	High Similarity	NPC262858
0.8736	High Similarity	NPC146554
0.8736	High Similarity	NPC474889
0.8721	High Similarity	NPC159046
0.8721	High Similarity	NPC233836
0.8721	High Similarity	NPC187376
0.8721	High Similarity	NPC478104
0.8706	High Similarity	NPC191965
0.8696	High Similarity	NPC208358
0.8696	High Similarity	NPC473510
0.869	High Similarity	NPC5280
0.869	High Similarity	NPC474789
0.869	High Similarity	NPC139206
0.869	High Similarity	NPC52108
0.8681	High Similarity	NPC141401
0.8681	High Similarity	NPC210337
0.8675	High Similarity	NPC474531
0.8667	High Similarity	NPC469599
0.8667	High Similarity	NPC279974
0.8659	High Similarity	NPC1319
0.8652	High Similarity	NPC470376
0.8652	High Similarity	NPC170220
0.8652	High Similarity	NPC141497
0.8652	High Similarity	NPC470375
0.8652	High Similarity	NPC107674
0.8642	High Similarity	NPC155986
0.8642	High Similarity	NPC214570
0.8642	High Similarity	NPC283619
0.8642	High Similarity	NPC198968
0.8642	High Similarity	NPC318495
0.8625	High Similarity	NPC230301
0.8625	High Similarity	NPC304309
0.8625	High Similarity	NPC285893
0.8625	High Similarity	NPC288035
0.8625	High Similarity	NPC134847
0.8625	High Similarity	NPC136188
0.8625	High Similarity	NPC22105
0.8625	High Similarity	NPC141071
0.8625	High Similarity	NPC257347
0.8625	High Similarity	NPC471723
0.8625	High Similarity	NPC162742
0.8625	High Similarity	NPC28657
0.8605	High Similarity	NPC137306
0.8605	High Similarity	NPC168231
0.8605	High Similarity	NPC325594
0.8605	High Similarity	NPC28252
0.8605	High Similarity	NPC55309
0.8605	High Similarity	NPC73038
0.8605	High Similarity	NPC286153
0.8605	High Similarity	NPC84121
0.8602	High Similarity	NPC475617
0.8602	High Similarity	NPC155974
0.8588	High Similarity	NPC124172
0.8588	High Similarity	NPC299963
0.8571	High Similarity	NPC472504
0.8571	High Similarity	NPC30166
0.8571	High Similarity	NPC471903
0.8571	High Similarity	NPC101462
0.8571	High Similarity	NPC120708
0.8571	High Similarity	NPC5985
0.8571	High Similarity	NPC470049
0.8556	High Similarity	NPC119562
0.8556	High Similarity	NPC476186
0.8556	High Similarity	NPC159410
0.8556	High Similarity	NPC279410
0.8554	High Similarity	NPC102253
0.8554	High Similarity	NPC236237
0.8554	High Similarity	NPC236112
0.8554	High Similarity	NPC322313
0.8539	High Similarity	NPC86266
0.8539	High Similarity	NPC212301
0.8539	High Similarity	NPC110657
0.8539	High Similarity	NPC297265
0.8537	High Similarity	NPC477522
0.8537	High Similarity	NPC6978
0.8537	High Similarity	NPC244385
0.8537	High Similarity	NPC473943
0.8537	High Similarity	NPC474216
0.8537	High Similarity	NPC285761
0.8537	High Similarity	NPC167037
0.8537	High Similarity	NPC87604
0.8537	High Similarity	NPC138621
0.8523	High Similarity	NPC77168
0.8523	High Similarity	NPC84271
0.8523	High Similarity	NPC102414
0.8523	High Similarity	NPC128496
0.8519	High Similarity	NPC46160
0.8519	High Similarity	NPC134330
0.8519	High Similarity	NPC129165
0.8519	High Similarity	NPC73875
0.8519	High Similarity	NPC202642
0.8519	High Similarity	NPC237460
0.8519	High Similarity	NPC113733
0.8511	High Similarity	NPC475344
0.8511	High Similarity	NPC476471
0.8495	Intermediate Similarity	NPC230546
0.8488	Intermediate Similarity	NPC266511
0.8488	Intermediate Similarity	NPC476602
0.8478	Intermediate Similarity	NPC108078
0.8471	Intermediate Similarity	NPC132386
0.8462	Intermediate Similarity	NPC470016
0.8462	Intermediate Similarity	NPC317586
0.8462	Intermediate Similarity	NPC69548
0.8462	Intermediate Similarity	NPC184848
0.8452	Intermediate Similarity	NPC82986
0.8452	Intermediate Similarity	NPC474759
0.8452	Intermediate Similarity	NPC470383
0.8452	Intermediate Similarity	NPC474752
0.8452	Intermediate Similarity	NPC7505
0.8452	Intermediate Similarity	NPC474683
0.8452	Intermediate Similarity	NPC474731
0.8444	Intermediate Similarity	NPC473678
0.8444	Intermediate Similarity	NPC214697
0.8444	Intermediate Similarity	NPC476304
0.8434	Intermediate Similarity	NPC143182
0.8434	Intermediate Similarity	NPC80530
0.8434	Intermediate Similarity	NPC28862
0.8434	Intermediate Similarity	NPC47982
0.8434	Intermediate Similarity	NPC84694
0.8434	Intermediate Similarity	NPC328714
0.8434	Intermediate Similarity	NPC109546
0.8434	Intermediate Similarity	NPC30986
0.8434	Intermediate Similarity	NPC209430
0.8434	Intermediate Similarity	NPC273410
0.8434	Intermediate Similarity	NPC81306
0.8427	Intermediate Similarity	NPC469400
0.8427	Intermediate Similarity	NPC474728
0.8427	Intermediate Similarity	NPC473269
0.8427	Intermediate Similarity	NPC78973
0.8421	Intermediate Similarity	NPC474124
0.8415	Intermediate Similarity	NPC34019
0.8409	Intermediate Similarity	NPC470612
0.8409	Intermediate Similarity	NPC470613
0.8395	Intermediate Similarity	NPC118508
0.8395	Intermediate Similarity	NPC121744
0.8395	Intermediate Similarity	NPC322353
0.8391	Intermediate Similarity	NPC264127
0.8391	Intermediate Similarity	NPC261266
0.8391	Intermediate Similarity	NPC24277
0.8391	Intermediate Similarity	NPC6391
0.8391	Intermediate Similarity	NPC125399
0.8387	Intermediate Similarity	NPC477813
0.8387	Intermediate Similarity	NPC477854
0.8387	Intermediate Similarity	NPC102426
0.8387	Intermediate Similarity	NPC300179
0.8387	Intermediate Similarity	NPC119036
0.8372	Intermediate Similarity	NPC221758
0.8372	Intermediate Similarity	NPC59453
0.8372	Intermediate Similarity	NPC33913
0.8372	Intermediate Similarity	NPC185568
0.8372	Intermediate Similarity	NPC474047
0.8372	Intermediate Similarity	NPC470077
0.8372	Intermediate Similarity	NPC478102
0.8372	Intermediate Similarity	NPC472265
0.8372	Intermediate Similarity	NPC205845
0.8372	Intermediate Similarity	NPC209802
0.837	Intermediate Similarity	NPC327788
0.837	Intermediate Similarity	NPC173272
0.8353	Intermediate Similarity	NPC49964
0.8353	Intermediate Similarity	NPC470614
0.8353	Intermediate Similarity	NPC256112
0.8353	Intermediate Similarity	NPC1272

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 NPC474970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	1301
0.2-0.3	4083
0.3-0.4	2495
0.4-0.5	623
0.5-0.6	186
0.6-0.7	155
0.7-0.8	159
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8652	High Similarity	NPD6399	Phase 3
0.8625	High Similarity	NPD6942	Approved
0.8625	High Similarity	NPD7339	Approved
0.8554	High Similarity	NPD7525	Registered
0.8372	Intermediate Similarity	NPD4786	Approved
0.8293	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD7638	Approved
0.814	Intermediate Similarity	NPD3667	Approved
0.8111	Intermediate Similarity	NPD5328	Approved
0.8105	Intermediate Similarity	NPD7639	Approved
0.8105	Intermediate Similarity	NPD7640	Approved
0.8068	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6402	Approved
0.8061	Intermediate Similarity	NPD5739	Approved
0.8061	Intermediate Similarity	NPD7128	Approved
0.8061	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD7645	Phase 2
0.7978	Intermediate Similarity	NPD3618	Phase 1
0.7957	Intermediate Similarity	NPD7748	Approved
0.7935	Intermediate Similarity	NPD7515	Phase 2
0.7935	Intermediate Similarity	NPD6079	Approved
0.7935	Intermediate Similarity	NPD8035	Phase 2
0.7935	Intermediate Similarity	NPD8034	Phase 2
0.7912	Intermediate Similarity	NPD6051	Approved
0.79	Intermediate Similarity	NPD6881	Approved
0.79	Intermediate Similarity	NPD7320	Approved
0.79	Intermediate Similarity	NPD6899	Approved
0.7895	Intermediate Similarity	NPD6084	Phase 2
0.7895	Intermediate Similarity	NPD6083	Phase 2
0.7831	Intermediate Similarity	NPD6926	Approved
0.7831	Intermediate Similarity	NPD6924	Approved
0.7822	Intermediate Similarity	NPD6372	Approved
0.7822	Intermediate Similarity	NPD6373	Approved
0.7802	Intermediate Similarity	NPD5737	Approved
0.7802	Intermediate Similarity	NPD6672	Approved
0.78	Intermediate Similarity	NPD5701	Approved
0.78	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD6409	Approved
0.7778	Intermediate Similarity	NPD6684	Approved
0.7778	Intermediate Similarity	NPD5330	Approved
0.7778	Intermediate Similarity	NPD7146	Approved
0.7778	Intermediate Similarity	NPD7521	Approved
0.7778	Intermediate Similarity	NPD7334	Approved
0.7745	Intermediate Similarity	NPD7102	Approved
0.7745	Intermediate Similarity	NPD7290	Approved
0.7745	Intermediate Similarity	NPD6883	Approved
0.7723	Intermediate Similarity	NPD6011	Approved
0.7708	Intermediate Similarity	NPD7902	Approved
0.767	Intermediate Similarity	NPD6869	Approved
0.767	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6650	Approved
0.767	Intermediate Similarity	NPD6617	Approved
0.767	Intermediate Similarity	NPD8130	Phase 1
0.767	Intermediate Similarity	NPD6649	Approved
0.767	Intermediate Similarity	NPD6847	Approved
0.766	Intermediate Similarity	NPD4202	Approved
0.7647	Intermediate Similarity	NPD6933	Approved
0.7647	Intermediate Similarity	NPD6012	Approved
0.7647	Intermediate Similarity	NPD6014	Approved
0.7647	Intermediate Similarity	NPD6013	Approved
0.764	Intermediate Similarity	NPD6695	Phase 3
0.7619	Intermediate Similarity	NPD4784	Approved
0.7619	Intermediate Similarity	NPD4785	Approved
0.7609	Intermediate Similarity	NPD6903	Approved
0.7609	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD4697	Phase 3
0.7604	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5222	Approved
0.7604	Intermediate Similarity	NPD5221	Approved
0.7596	Intermediate Similarity	NPD6882	Approved
0.7596	Intermediate Similarity	NPD8297	Approved
0.759	Intermediate Similarity	NPD7152	Approved
0.759	Intermediate Similarity	NPD7150	Approved
0.759	Intermediate Similarity	NPD4243	Approved
0.759	Intermediate Similarity	NPD7151	Approved
0.7561	Intermediate Similarity	NPD6922	Approved
0.7561	Intermediate Similarity	NPD6923	Approved
0.7556	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3665	Phase 1
0.7556	Intermediate Similarity	NPD3666	Approved
0.7556	Intermediate Similarity	NPD3133	Approved
0.7556	Intermediate Similarity	NPD3668	Phase 3
0.7553	Intermediate Similarity	NPD7637	Suspended
0.7526	Intermediate Similarity	NPD5173	Approved
0.7526	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD4748	Discontinued
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7115	Discovery
0.747	Intermediate Similarity	NPD7143	Approved
0.747	Intermediate Similarity	NPD7144	Approved
0.7449	Intermediate Similarity	NPD5696	Approved
0.7449	Intermediate Similarity	NPD4225	Approved
0.7442	Intermediate Similarity	NPD6117	Approved
0.74	Intermediate Similarity	NPD7632	Discontinued
0.7396	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7900	Approved
0.7391	Intermediate Similarity	NPD6098	Approved
0.7386	Intermediate Similarity	NPD6929	Approved
0.7386	Intermediate Similarity	NPD4195	Approved
0.7383	Intermediate Similarity	NPD6868	Approved
0.7374	Intermediate Similarity	NPD5286	Approved
0.7374	Intermediate Similarity	NPD4700	Approved
0.7374	Intermediate Similarity	NPD4696	Approved
0.7374	Intermediate Similarity	NPD5285	Approved
0.7368	Intermediate Similarity	NPD6411	Approved
0.7356	Intermediate Similarity	NPD6116	Phase 1
0.7353	Intermediate Similarity	NPD6008	Approved
0.734	Intermediate Similarity	NPD6904	Approved
0.734	Intermediate Similarity	NPD6080	Approved
0.734	Intermediate Similarity	NPD6673	Approved
0.734	Intermediate Similarity	NPD4753	Phase 2
0.7312	Intermediate Similarity	NPD7524	Approved
0.7312	Intermediate Similarity	NPD7750	Discontinued
0.7303	Intermediate Similarity	NPD6931	Approved
0.7303	Intermediate Similarity	NPD6930	Phase 2
0.7303	Intermediate Similarity	NPD7509	Discontinued
0.73	Intermediate Similarity	NPD5223	Approved
0.7273	Intermediate Similarity	NPD6114	Approved
0.7273	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6118	Approved
0.7273	Intermediate Similarity	NPD6115	Approved
0.7248	Intermediate Similarity	NPD6335	Approved
0.7228	Intermediate Similarity	NPD5226	Approved
0.7228	Intermediate Similarity	NPD5224	Approved
0.7228	Intermediate Similarity	NPD4633	Approved
0.7228	Intermediate Similarity	NPD5225	Approved
0.7228	Intermediate Similarity	NPD5211	Phase 2
0.7222	Intermediate Similarity	NPD6274	Approved
0.7209	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5279	Phase 3
0.7196	Intermediate Similarity	NPD4632	Approved
0.7182	Intermediate Similarity	NPD7100	Approved
0.7182	Intermediate Similarity	NPD7101	Approved
0.7159	Intermediate Similarity	NPD6932	Approved
0.7159	Intermediate Similarity	NPD6925	Approved
0.7159	Intermediate Similarity	NPD5776	Phase 2
0.7158	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6101	Approved
0.7157	Intermediate Similarity	NPD5174	Approved
0.7157	Intermediate Similarity	NPD5175	Approved
0.7157	Intermediate Similarity	NPD4754	Approved
0.7156	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD4221	Approved
0.7126	Intermediate Similarity	NPD5275	Approved
0.7126	Intermediate Similarity	NPD4190	Phase 3
0.71	Intermediate Similarity	NPD5290	Discontinued
0.7097	Intermediate Similarity	NPD5329	Approved
0.7091	Intermediate Similarity	NPD7327	Approved
0.7091	Intermediate Similarity	NPD6314	Approved
0.7091	Intermediate Similarity	NPD6313	Approved
0.7091	Intermediate Similarity	NPD7328	Approved
0.7087	Intermediate Similarity	NPD5141	Approved
0.7079	Intermediate Similarity	NPD7145	Approved
0.7054	Intermediate Similarity	NPD6908	Approved
0.7054	Intermediate Similarity	NPD6909	Approved
0.7054	Intermediate Similarity	NPD8033	Approved
0.7053	Intermediate Similarity	NPD5208	Approved
0.7041	Intermediate Similarity	NPD6001	Approved
0.7027	Intermediate Similarity	NPD7516	Approved
0.7021	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4767	Approved
0.7019	Intermediate Similarity	NPD4768	Approved
0.701	Intermediate Similarity	NPD5693	Phase 1
0.701	Intermediate Similarity	NPD5284	Approved
0.701	Intermediate Similarity	NPD7087	Discontinued
0.701	Intermediate Similarity	NPD6050	Approved
0.701	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD6683	Phase 2
0.6989	Remote Similarity	NPD4197	Approved
0.697	Remote Similarity	NPD4629	Approved
0.697	Remote Similarity	NPD5210	Approved
0.6964	Remote Similarity	NPD8377	Approved
0.6964	Remote Similarity	NPD6319	Approved
0.6964	Remote Similarity	NPD8294	Approved
0.6952	Remote Similarity	NPD6412	Phase 2
0.6947	Remote Similarity	NPD3573	Approved
0.6941	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD8264	Approved
0.693	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD7514	Phase 3
0.6915	Remote Similarity	NPD6893	Approved
0.6907	Remote Similarity	NPD5692	Phase 3
0.6903	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8378	Approved
0.6903	Remote Similarity	NPD8335	Approved
0.6903	Remote Similarity	NPD8380	Approved
0.6903	Remote Similarity	NPD7503	Approved
0.6903	Remote Similarity	NPD8379	Approved
0.6903	Remote Similarity	NPD5983	Phase 2
0.6903	Remote Similarity	NPD8296	Approved
0.6889	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4729	Approved
0.6887	Remote Similarity	NPD5168	Approved
0.6887	Remote Similarity	NPD5128	Approved
0.6887	Remote Similarity	NPD4730	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