NPASS Compound

Structure

NPC474807 OpenBabel07101718242D 31 34 0 0 1 0 0 0 0 0999 V2000 -4.2456 -0.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5328 0.3975 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 -1.0522 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 0.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8855 0.9328 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 4.3301 -1.5000 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 -2.2382 1.4680 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 0.8660 0.5000 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 -0.9511 -1.3090 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 -4.5546 0.1896 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 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 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 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 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 -1.2601 1.2601 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 1.4013 1.0181 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 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 1.5691 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 6 1 0 0 0 0 5 11 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 26 1 0 0 0 0 12 25 1 0 0 0 0 13 27 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 28 1 0 0 0 0 18 25 1 0 0 0 0 19 29 2 0 0 0 0 20 8 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 1 6 0 0 0 22 27 1 6 0 0 0 23 24 1 0 0 0 0 23 30 2 0 0 0 0 24 26 1 0 0 0 0 24 27 1 6 0 0 0 25 3 1 6 0 0 0 26 4 1 1 0 0 0 26 31 1 0 0 0 0 27 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	465.937
LogP:	4.431
LogD:	4.041
LogS:	-4.387
# Rotatable Bonds:	6
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.605
Synthetic Accessibility Score:	4.977
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.614
MDCK Permeability:	2.3555339794256724e-05
Pgp-inhibitor:	0.116
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.908
Plasma Protein Binding (PPB):	88.22603607177734%
Volume Distribution (VD):	0.568
Pgp-substrate:	4.883934020996094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.612
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.624

ADMET: Excretion

Clearance (CL):	12.993
Half-life (T1/2):	0.373

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.86
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.83
Carcinogencity:	0.872
Eye Corrosion:	0.483
Eye Irritation:	0.153
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC474807

Natural Product ID:	NPC474807
*Common Name:**	(8R,9S,10R,13R,14S,17S)-13-(Hydroxymethyl)-17-[(2S)-2-Hydroxy-6-Methylheptan-2-Yl]-10-Methyl-7,8,9,11,12,14,15,17-Octahydro-6H-Cyclopenta[A]Phenanthrene-3,16-Dione
IUPAC Name:	(8R,9S,10R,13R,14S,17S)-13-(hydroxymethyl)-17-[(2S)-2-hydroxy-6-methylheptan-2-yl]-10-methyl-7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthrene-3,16-dione
Synonyms:
Standard InCHIKey:	HYVXADHHWJJRCX-HIKPHUAPSA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-17(2)6-5-11-26(4,31)24-23(30)15-22-20-8-7-18-14-19(29)9-12-25(18,3)21(20)10-13-27(22,24)16-28/h9,12,14,17,20-22,24,28,31H,5-8,10-11,13,15-16H2,1-4H3/t20-,21+,22+,24-,25+,26+,27-/m1/s1
SMILES:	CC(C)CCCC(C)(C1C(=O)CC2C1(CCC3C2CCC4=CC(=O)C=CC34C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483446
PubChem CID:	21602075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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
NPO20574	Antipathes subpinnata	Species	Antipathidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1350615]
NPO20574	Antipathes subpinnata	Species	Antipathidae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	139.4	ug.mL-1	PMID[476928]

☑ 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 NPC474807 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	173
0.1-0.2	1096
0.2-0.3	5177
0.3-0.4	12296
0.4-0.5	9557
0.5-0.6	6761
0.6-0.7	5185
0.7-0.8	2185
0.8-0.85	201
0.85-0.9	64
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8989	High Similarity	NPC477943
0.8977	High Similarity	NPC93778
0.8966	High Similarity	NPC469948
0.8851	High Similarity	NPC85774
0.8851	High Similarity	NPC214043
0.8764	High Similarity	NPC96496
0.8764	High Similarity	NPC58063
0.8667	High Similarity	NPC470417
0.8652	High Similarity	NPC474732
0.8652	High Similarity	NPC474733
0.8652	High Similarity	NPC31564
0.8652	High Similarity	NPC145879
0.8652	High Similarity	NPC474778
0.8636	High Similarity	NPC473246
0.8636	High Similarity	NPC237712
0.8605	High Similarity	NPC472478
0.8602	High Similarity	NPC8993
0.8587	High Similarity	NPC475806
0.8587	High Similarity	NPC272746
0.8587	High Similarity	NPC19114
0.8571	High Similarity	NPC472477
0.8571	High Similarity	NPC262043
0.8571	High Similarity	NPC326627
0.8571	High Similarity	NPC186688
0.8571	High Similarity	NPC1015
0.8571	High Similarity	NPC310010
0.8571	High Similarity	NPC31985
0.8571	High Similarity	NPC472475
0.8557	High Similarity	NPC87351
0.8556	High Similarity	NPC90652
0.8556	High Similarity	NPC472481
0.8556	High Similarity	NPC136548
0.8556	High Similarity	NPC475740
0.8556	High Similarity	NPC472484
0.8556	High Similarity	NPC472482
0.8542	High Similarity	NPC144956
0.8539	High Similarity	NPC29447
0.8539	High Similarity	NPC474218
0.8506	High Similarity	NPC116797
0.8495	Intermediate Similarity	NPC233118
0.8495	Intermediate Similarity	NPC475255
0.8495	Intermediate Similarity	NPC474736
0.8478	Intermediate Similarity	NPC171441
0.8478	Intermediate Similarity	NPC320026
0.8478	Intermediate Similarity	NPC129913
0.8469	Intermediate Similarity	NPC311612
0.8462	Intermediate Similarity	NPC471793
0.8462	Intermediate Similarity	NPC471724
0.8462	Intermediate Similarity	NPC53911
0.8462	Intermediate Similarity	NPC328313
0.8462	Intermediate Similarity	NPC471791
0.8462	Intermediate Similarity	NPC328539
0.8444	Intermediate Similarity	NPC222613
0.8444	Intermediate Similarity	NPC327115
0.8444	Intermediate Similarity	NPC118648
0.8444	Intermediate Similarity	NPC475022
0.8438	Intermediate Similarity	NPC147954
0.8427	Intermediate Similarity	NPC82902
0.8427	Intermediate Similarity	NPC161423
0.8427	Intermediate Similarity	NPC227064
0.8427	Intermediate Similarity	NPC476412
0.8427	Intermediate Similarity	NPC321187
0.8427	Intermediate Similarity	NPC59453
0.8427	Intermediate Similarity	NPC221758
0.8427	Intermediate Similarity	NPC58841
0.8427	Intermediate Similarity	NPC33913
0.8427	Intermediate Similarity	NPC472265
0.8427	Intermediate Similarity	NPC329043
0.8421	Intermediate Similarity	NPC249954
0.8421	Intermediate Similarity	NPC29152
0.8409	Intermediate Similarity	NPC193347
0.8404	Intermediate Similarity	NPC111015
0.8404	Intermediate Similarity	NPC473172
0.84	Intermediate Similarity	NPC43285
0.84	Intermediate Similarity	NPC58370
0.8391	Intermediate Similarity	NPC2482
0.8387	Intermediate Similarity	NPC168027
0.8387	Intermediate Similarity	NPC473998
0.8387	Intermediate Similarity	NPC185936
0.8387	Intermediate Similarity	NPC154101
0.8372	Intermediate Similarity	NPC82635
0.837	Intermediate Similarity	NPC275740
0.837	Intermediate Similarity	NPC474245
0.837	Intermediate Similarity	NPC26959
0.837	Intermediate Similarity	NPC2983
0.837	Intermediate Similarity	NPC474570
0.837	Intermediate Similarity	NPC473999
0.837	Intermediate Similarity	NPC32830
0.837	Intermediate Similarity	NPC268406
0.837	Intermediate Similarity	NPC119416
0.837	Intermediate Similarity	NPC309603
0.837	Intermediate Similarity	NPC86319
0.8352	Intermediate Similarity	NPC317590
0.8352	Intermediate Similarity	NPC136948
0.8351	Intermediate Similarity	NPC474720
0.8351	Intermediate Similarity	NPC154072
0.8333	Intermediate Similarity	NPC18509
0.8333	Intermediate Similarity	NPC156546
0.8333	Intermediate Similarity	NPC471224
0.8333	Intermediate Similarity	NPC107243
0.8333	Intermediate Similarity	NPC473161
0.8333	Intermediate Similarity	NPC476426
0.8333	Intermediate Similarity	NPC57416
0.8333	Intermediate Similarity	NPC470574
0.8333	Intermediate Similarity	NPC108078
0.8316	Intermediate Similarity	NPC263347
0.8316	Intermediate Similarity	NPC271195
0.8316	Intermediate Similarity	NPC259286
0.8316	Intermediate Similarity	NPC472485
0.8315	Intermediate Similarity	NPC477373
0.8298	Intermediate Similarity	NPC472930
0.8283	Intermediate Similarity	NPC111323
0.8283	Intermediate Similarity	NPC117185
0.828	Intermediate Similarity	NPC48010
0.828	Intermediate Similarity	NPC472476
0.828	Intermediate Similarity	NPC191684
0.828	Intermediate Similarity	NPC85173
0.828	Intermediate Similarity	NPC126993
0.8276	Intermediate Similarity	NPC472490
0.8276	Intermediate Similarity	NPC215843
0.8265	Intermediate Similarity	NPC476223
0.8265	Intermediate Similarity	NPC472924
0.8265	Intermediate Similarity	NPC476240
0.8265	Intermediate Similarity	NPC224720
0.8261	Intermediate Similarity	NPC143767
0.8261	Intermediate Similarity	NPC472483
0.8261	Intermediate Similarity	NPC471722
0.8261	Intermediate Similarity	NPC131470
0.8247	Intermediate Similarity	NPC114274
0.8247	Intermediate Similarity	NPC103051
0.8242	Intermediate Similarity	NPC194417
0.8242	Intermediate Similarity	NPC472479
0.8242	Intermediate Similarity	NPC469994
0.8242	Intermediate Similarity	NPC473168
0.8242	Intermediate Similarity	NPC51014
0.8242	Intermediate Similarity	NPC72133
0.8235	Intermediate Similarity	NPC470257
0.8229	Intermediate Similarity	NPC192428
0.8229	Intermediate Similarity	NPC473164
0.8229	Intermediate Similarity	NPC49371
0.8229	Intermediate Similarity	NPC471463
0.8222	Intermediate Similarity	NPC144258
0.8222	Intermediate Similarity	NPC472480
0.8218	Intermediate Similarity	NPC185
0.8211	Intermediate Similarity	NPC292793
0.8211	Intermediate Similarity	NPC67831
0.8211	Intermediate Similarity	NPC299100
0.8211	Intermediate Similarity	NPC174051
0.8211	Intermediate Similarity	NPC196485
0.8211	Intermediate Similarity	NPC245972
0.8202	Intermediate Similarity	NPC320514
0.8202	Intermediate Similarity	NPC151519
0.82	Intermediate Similarity	NPC255309
0.82	Intermediate Similarity	NPC235889
0.8191	Intermediate Similarity	NPC204341
0.8182	Intermediate Similarity	NPC476809
0.8182	Intermediate Similarity	NPC477915
0.8182	Intermediate Similarity	NPC45495
0.8172	Intermediate Similarity	NPC123912
0.8172	Intermediate Similarity	NPC472489
0.8172	Intermediate Similarity	NPC184663
0.8172	Intermediate Similarity	NPC76879
0.8172	Intermediate Similarity	NPC54689
0.8172	Intermediate Similarity	NPC477973
0.8163	Intermediate Similarity	NPC287833
0.8163	Intermediate Similarity	NPC112167
0.8163	Intermediate Similarity	NPC476274
0.8155	Intermediate Similarity	NPC235077
0.8152	Intermediate Similarity	NPC141292
0.8152	Intermediate Similarity	NPC99909
0.8144	Intermediate Similarity	NPC472690
0.8144	Intermediate Similarity	NPC477267
0.8144	Intermediate Similarity	NPC477268
0.8144	Intermediate Similarity	NPC472689
0.8132	Intermediate Similarity	NPC474083
0.8132	Intermediate Similarity	NPC197823
0.8125	Intermediate Similarity	NPC469599
0.8125	Intermediate Similarity	NPC88310
0.8125	Intermediate Similarity	NPC472824
0.8125	Intermediate Similarity	NPC472932
0.8125	Intermediate Similarity	NPC180950
0.8125	Intermediate Similarity	NPC473170
0.8125	Intermediate Similarity	NPC280725
0.8125	Intermediate Similarity	NPC476174
0.8119	Intermediate Similarity	NPC50692
0.8119	Intermediate Similarity	NPC49958
0.8119	Intermediate Similarity	NPC296945
0.8119	Intermediate Similarity	NPC150531
0.8119	Intermediate Similarity	NPC96377
0.8119	Intermediate Similarity	NPC476027
0.8119	Intermediate Similarity	NPC181265
0.8119	Intermediate Similarity	NPC48733
0.8119	Intermediate Similarity	NPC166607
0.8119	Intermediate Similarity	NPC171137
0.8119	Intermediate Similarity	NPC152695
0.8119	Intermediate Similarity	NPC214264
0.8119	Intermediate Similarity	NPC302607
0.8119	Intermediate Similarity	NPC85829
0.8119	Intermediate Similarity	NPC319077
0.8119	Intermediate Similarity	NPC97202

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 NPC474807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1392
0.2-0.3	4001
0.3-0.4	2470
0.4-0.5	650
0.5-0.6	168
0.6-0.7	127
0.7-0.8	128
0.8-0.85	41
0.85-0.9	23
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8791	High Similarity	NPD6079	Approved
0.871	High Similarity	NPD4629	Approved
0.871	High Similarity	NPD5210	Approved
0.8652	High Similarity	NPD3574	Clinical (unspecified phase)
0.8571	High Similarity	NPD4753	Phase 2
0.8571	High Similarity	NPD5328	Approved
0.8542	High Similarity	NPD5286	Approved
0.8542	High Similarity	NPD5285	Approved
0.8542	High Similarity	NPD4696	Approved
0.8454	Intermediate Similarity	NPD5223	Approved
0.8444	Intermediate Similarity	NPD3618	Phase 1
0.8427	Intermediate Similarity	NPD4786	Approved
0.8427	Intermediate Similarity	NPD3133	Approved
0.8427	Intermediate Similarity	NPD3665	Phase 1
0.8427	Intermediate Similarity	NPD3666	Approved
0.8421	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD5222	Approved
0.8421	Intermediate Similarity	NPD5221	Approved
0.8409	Intermediate Similarity	NPD4221	Approved
0.8409	Intermediate Similarity	NPD4223	Phase 3
0.8367	Intermediate Similarity	NPD5224	Approved
0.8367	Intermediate Similarity	NPD5226	Approved
0.8367	Intermediate Similarity	NPD5225	Approved
0.8367	Intermediate Similarity	NPD4633	Approved
0.8367	Intermediate Similarity	NPD5211	Phase 2
0.8333	Intermediate Similarity	NPD5329	Approved
0.8333	Intermediate Similarity	NPD5173	Approved
0.8333	Intermediate Similarity	NPD4755	Approved
0.8298	Intermediate Similarity	NPD4202	Approved
0.8283	Intermediate Similarity	NPD5174	Approved
0.8283	Intermediate Similarity	NPD5175	Approved
0.8242	Intermediate Similarity	NPD5690	Phase 2
0.8229	Intermediate Similarity	NPD4697	Phase 3
0.8222	Intermediate Similarity	NPD4197	Approved
0.8202	Intermediate Similarity	NPD3667	Approved
0.82	Intermediate Similarity	NPD5141	Approved
0.8191	Intermediate Similarity	NPD5281	Approved
0.8191	Intermediate Similarity	NPD5284	Approved
0.8163	Intermediate Similarity	NPD4700	Approved
0.8155	Intermediate Similarity	NPD4634	Approved
0.8144	Intermediate Similarity	NPD6083	Phase 2
0.8144	Intermediate Similarity	NPD6084	Phase 2
0.8137	Intermediate Similarity	NPD6899	Approved
0.8137	Intermediate Similarity	NPD6881	Approved
0.8111	Intermediate Similarity	NPD4788	Approved
0.8105	Intermediate Similarity	NPD6399	Phase 3
0.8077	Intermediate Similarity	NPD6650	Approved
0.8077	Intermediate Similarity	NPD6649	Approved
0.8068	Intermediate Similarity	NPD4195	Approved
0.8043	Intermediate Similarity	NPD4689	Approved
0.8043	Intermediate Similarity	NPD4138	Approved
0.8043	Intermediate Similarity	NPD5279	Phase 3
0.8043	Intermediate Similarity	NPD4688	Approved
0.8043	Intermediate Similarity	NPD4693	Phase 3
0.8043	Intermediate Similarity	NPD4690	Approved
0.8043	Intermediate Similarity	NPD5205	Approved
0.8039	Intermediate Similarity	NPD5697	Approved
0.7981	Intermediate Similarity	NPD7290	Approved
0.7981	Intermediate Similarity	NPD7102	Approved
0.7981	Intermediate Similarity	NPD6883	Approved
0.7961	Intermediate Similarity	NPD6011	Approved
0.7961	Intermediate Similarity	NPD4730	Approved
0.7961	Intermediate Similarity	NPD4729	Approved
0.7941	Intermediate Similarity	NPD6675	Approved
0.7941	Intermediate Similarity	NPD6402	Approved
0.7941	Intermediate Similarity	NPD7128	Approved
0.7941	Intermediate Similarity	NPD5739	Approved
0.7921	Intermediate Similarity	NPD4754	Approved
0.7905	Intermediate Similarity	NPD6869	Approved
0.7905	Intermediate Similarity	NPD6847	Approved
0.7905	Intermediate Similarity	NPD6617	Approved
0.7905	Intermediate Similarity	NPD8130	Phase 1
0.7885	Intermediate Similarity	NPD6014	Approved
0.7885	Intermediate Similarity	NPD6372	Approved
0.7885	Intermediate Similarity	NPD6373	Approved
0.7885	Intermediate Similarity	NPD6012	Approved
0.7885	Intermediate Similarity	NPD6013	Approved
0.7879	Intermediate Similarity	NPD5696	Approved
0.7872	Intermediate Similarity	NPD6672	Approved
0.7872	Intermediate Similarity	NPD5737	Approved
0.7849	Intermediate Similarity	NPD5280	Approved
0.7849	Intermediate Similarity	NPD4694	Approved
0.783	Intermediate Similarity	NPD6882	Approved
0.783	Intermediate Similarity	NPD8297	Approved
0.781	Intermediate Similarity	NPD5249	Phase 3
0.781	Intermediate Similarity	NPD5247	Approved
0.781	Intermediate Similarity	NPD5248	Approved
0.781	Intermediate Similarity	NPD5250	Approved
0.781	Intermediate Similarity	NPD5135	Approved
0.781	Intermediate Similarity	NPD5169	Approved
0.781	Intermediate Similarity	NPD5251	Approved
0.781	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD5128	Approved
0.7788	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD4695	Discontinued
0.7767	Intermediate Similarity	NPD4768	Approved
0.7767	Intermediate Similarity	NPD4767	Approved
0.7755	Intermediate Similarity	NPD5695	Phase 3
0.7753	Intermediate Similarity	NPD3617	Approved
0.7736	Intermediate Similarity	NPD5216	Approved
0.7736	Intermediate Similarity	NPD5127	Approved
0.7736	Intermediate Similarity	NPD5215	Approved
0.7736	Intermediate Similarity	NPD5217	Approved
0.7706	Intermediate Similarity	NPD7115	Discovery
0.7692	Intermediate Similarity	NPD5701	Approved
0.766	Intermediate Similarity	NPD7334	Approved
0.766	Intermediate Similarity	NPD4623	Approved
0.766	Intermediate Similarity	NPD6409	Approved
0.766	Intermediate Similarity	NPD4519	Discontinued
0.766	Intermediate Similarity	NPD5330	Approved
0.766	Intermediate Similarity	NPD7146	Approved
0.766	Intermediate Similarity	NPD6684	Approved
0.766	Intermediate Similarity	NPD7521	Approved
0.7658	Intermediate Similarity	NPD6054	Approved
0.7647	Intermediate Similarity	NPD5091	Approved
0.7634	Intermediate Similarity	NPD3668	Phase 3
0.7629	Intermediate Similarity	NPD7515	Phase 2
0.7619	Intermediate Similarity	NPD5168	Approved
0.7604	Intermediate Similarity	NPD6080	Approved
0.7604	Intermediate Similarity	NPD6904	Approved
0.7604	Intermediate Similarity	NPD6673	Approved
0.7593	Intermediate Similarity	NPD4632	Approved
0.7582	Intermediate Similarity	NPD7525	Registered
0.7576	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4747	Approved
0.7558	Intermediate Similarity	NPD4691	Approved
0.7523	Intermediate Similarity	NPD5167	Approved
0.7522	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD4058	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6319	Approved
0.7477	Intermediate Similarity	NPD6335	Approved
0.7442	Intermediate Similarity	NPD4137	Phase 3
0.7434	Intermediate Similarity	NPD6015	Approved
0.7434	Intermediate Similarity	NPD6016	Approved
0.7426	Intermediate Similarity	NPD7902	Approved
0.7416	Intermediate Similarity	NPD7339	Approved
0.7416	Intermediate Similarity	NPD6942	Approved
0.7411	Intermediate Similarity	NPD4522	Approved
0.7411	Intermediate Similarity	NPD7101	Approved
0.7411	Intermediate Similarity	NPD7100	Approved
0.7391	Intermediate Similarity	NPD7492	Approved
0.7387	Intermediate Similarity	NPD6009	Approved
0.7387	Intermediate Similarity	NPD6317	Approved
0.7368	Intermediate Similarity	NPD5988	Approved
0.7358	Intermediate Similarity	NPD6412	Phase 2
0.7347	Intermediate Similarity	NPD5207	Approved
0.7347	Intermediate Similarity	NPD4096	Approved
0.7345	Intermediate Similarity	NPD6059	Approved
0.7328	Intermediate Similarity	NPD6616	Approved
0.7321	Intermediate Similarity	NPD6313	Approved
0.7321	Intermediate Similarity	NPD6314	Approved
0.732	Intermediate Similarity	NPD5208	Approved
0.732	Intermediate Similarity	NPD4518	Approved
0.7312	Intermediate Similarity	NPD4139	Approved
0.7312	Intermediate Similarity	NPD4692	Approved
0.7303	Intermediate Similarity	NPD4784	Approved
0.7303	Intermediate Similarity	NPD5733	Approved
0.7303	Intermediate Similarity	NPD4785	Approved
0.7303	Intermediate Similarity	NPD4687	Approved
0.73	Intermediate Similarity	NPD7748	Approved
0.7297	Intermediate Similarity	NPD6274	Approved
0.7297	Intermediate Similarity	NPD6868	Approved
0.7292	Intermediate Similarity	NPD6098	Approved
0.7281	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5693	Phase 1
0.7273	Intermediate Similarity	NPD4243	Approved
0.7273	Intermediate Similarity	NPD6050	Approved
0.7273	Intermediate Similarity	NPD5694	Approved
0.7265	Intermediate Similarity	NPD7078	Approved
0.7264	Intermediate Similarity	NPD6008	Approved
0.7216	Intermediate Similarity	NPD3573	Approved
0.7203	Intermediate Similarity	NPD7736	Approved
0.72	Intermediate Similarity	NPD5133	Approved
0.7188	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5363	Approved
0.7172	Intermediate Similarity	NPD5692	Phase 3
0.7172	Intermediate Similarity	NPD5785	Approved
0.7155	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5983	Phase 2
0.7129	Intermediate Similarity	NPD6001	Approved
0.7129	Intermediate Similarity	NPD7900	Approved
0.7129	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5369	Approved
0.7111	Intermediate Similarity	NPD6926	Approved
0.7111	Intermediate Similarity	NPD6924	Approved
0.71	Intermediate Similarity	NPD8035	Phase 2
0.71	Intermediate Similarity	NPD6411	Approved
0.71	Intermediate Similarity	NPD8034	Phase 2
0.7079	Intermediate Similarity	NPD5276	Approved
0.7071	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6614	Approved
0.7034	Intermediate Similarity	NPD6336	Discontinued
0.7019	Intermediate Similarity	NPD7638	Approved
0.699	Remote Similarity	NPD7614	Phase 1
0.6989	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6908	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