NPASS Compound

Structure

NPC474327 OpenBabel07101718182D 34 38 0 0 1 0 0 0 0 0999 V2000 -5.8308 1.6136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1909 -0.0806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 2.0000 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 -1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 -0.7044 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 -4.2346 -0.4965 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5218 0.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 0.0388 0.0000 C 0 0 3 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5436 0.4546 0.0000 C 0 0 1 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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8963 0.9898 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 1.7321 2.0000 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7024 -1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2272 1.7330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 1.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 20 2 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 16 30 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 6 0 0 0 22 17 1 1 0 0 0 22 34 1 0 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 25 29 1 1 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.32
Volume:	509.269
LogP:	5.757
LogD:	4.468
LogS:	-5.749
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.06
Fsp3:	0.8
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:	-4.976
MDCK Permeability:	2.3860882720327936e-05
Pgp-inhibitor:	0.948
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.798
Plasma Protein Binding (PPB):	84.5345687866211%
Volume Distribution (VD):	1.312
Pgp-substrate:	12.307351112365723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.581
CYP2C19-inhibitor:	0.171
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.215
CYP2C9-substrate:	0.295
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.799

ADMET: Excretion

Clearance (CL):	9.692
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.103
Carcinogencity:	0.357
Eye Corrosion:	0.014
Eye Irritation:	0.021
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC474327

Natural Product ID:	NPC474327
*Common Name:**	Dubione B
IUPAC Name:	(6S)-3-[(5R,9R,10R,13S,14S,16S,17S)-16-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-prop-1-en-2-yloxan-2-one
Synonyms:
Standard InCHIKey:	YCJCYIJUVKYWES-BFEFRAHYSA-N
Standard InCHI:	InChI=1S/C30H44O4/c1-17(2)22-10-8-18(26(33)34-22)25-21(31)16-30(7)20-9-11-23-27(3,4)24(32)13-14-28(23,5)19(20)12-15-29(25,30)6/h9,18-19,21-23,25,31H,1,8,10-16H2,2-7H3/t18?,19-,21-,22-,23-,25+,28+,29-,30+/m0/s1
SMILES:	CC(=C)C1CCC(C(=O)O1)C2C(CC3(C2(CCC4C3=CCC5C4(CCC(=O)C5(C)C)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465316
PubChem CID:	44567121
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
NPO18596	Melia dubia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502333]
NPO18596	Melia dubia	Species	Meliaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	20.5	ug ml-1	PMID[557215]

☑ 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 NPC474327 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	197
0.1-0.2	1197
0.2-0.3	4771
0.3-0.4	11344
0.4-0.5	9977
0.5-0.6	5883
0.6-0.7	5785
0.7-0.8	3305
0.8-0.85	205
0.85-0.9	32
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.914	High Similarity	NPC154101
0.9072	High Similarity	NPC218383
0.9053	High Similarity	NPC469599
0.8889	High Similarity	NPC185530
0.8866	High Similarity	NPC107243
0.8866	High Similarity	NPC475894
0.8866	High Similarity	NPC57416
0.88	High Similarity	NPC26478
0.88	High Similarity	NPC140723
0.8776	High Similarity	NPC176845
0.8725	High Similarity	NPC144459
0.8723	High Similarity	NPC54689
0.87	High Similarity	NPC473928
0.8646	High Similarity	NPC470375
0.8646	High Similarity	NPC152897
0.8646	High Similarity	NPC243866
0.8646	High Similarity	NPC66429
0.8646	High Similarity	NPC470376
0.8627	High Similarity	NPC60681
0.8627	High Similarity	NPC231530
0.8627	High Similarity	NPC278628
0.8617	High Similarity	NPC294480
0.8614	High Similarity	NPC236390
0.8586	High Similarity	NPC271387
0.8586	High Similarity	NPC153792
0.8571	High Similarity	NPC155676
0.8529	High Similarity	NPC149124
0.8529	High Similarity	NPC75531
0.8529	High Similarity	NPC235889
0.8526	High Similarity	NPC477943
0.8515	High Similarity	NPC195290
0.8515	High Similarity	NPC136289
0.8515	High Similarity	NPC204450
0.8511	High Similarity	NPC312215
0.8511	High Similarity	NPC317590
0.85	High Similarity	NPC83709
0.85	High Similarity	NPC476274
0.8495	Intermediate Similarity	NPC474218
0.8491	Intermediate Similarity	NPC100267
0.8491	Intermediate Similarity	NPC475524
0.8469	Intermediate Similarity	NPC263347
0.8469	Intermediate Similarity	NPC20546
0.8469	Intermediate Similarity	NPC69548
0.8469	Intermediate Similarity	NPC184848
0.8462	Intermediate Similarity	NPC94529
0.8462	Intermediate Similarity	NPC177064
0.8454	Intermediate Similarity	NPC206810
0.8447	Intermediate Similarity	NPC196528
0.8447	Intermediate Similarity	NPC181265
0.8421	Intermediate Similarity	NPC28227
0.8421	Intermediate Similarity	NPC183546
0.8416	Intermediate Similarity	NPC224720
0.8416	Intermediate Similarity	NPC81530
0.8416	Intermediate Similarity	NPC476240
0.8416	Intermediate Similarity	NPC476223
0.8404	Intermediate Similarity	NPC212843
0.8404	Intermediate Similarity	NPC472505
0.8404	Intermediate Similarity	NPC469994
0.84	Intermediate Similarity	NPC197386
0.84	Intermediate Similarity	NPC477813
0.8387	Intermediate Similarity	NPC82902
0.8384	Intermediate Similarity	NPC322063
0.8384	Intermediate Similarity	NPC42042
0.8381	Intermediate Similarity	NPC258543
0.8381	Intermediate Similarity	NPC241927
0.8365	Intermediate Similarity	NPC475294
0.8364	Intermediate Similarity	NPC475041
0.8351	Intermediate Similarity	NPC23434
0.8351	Intermediate Similarity	NPC150383
0.8351	Intermediate Similarity	NPC218301
0.835	Intermediate Similarity	NPC137657
0.835	Intermediate Similarity	NPC29705
0.8333	Intermediate Similarity	NPC476733
0.8333	Intermediate Similarity	NPC471398
0.8333	Intermediate Similarity	NPC170615
0.8333	Intermediate Similarity	NPC215029
0.8333	Intermediate Similarity	NPC474570
0.8333	Intermediate Similarity	NPC155479
0.8333	Intermediate Similarity	NPC474679
0.8333	Intermediate Similarity	NPC56498
0.8333	Intermediate Similarity	NPC473647
0.8318	Intermediate Similarity	NPC221144
0.8317	Intermediate Similarity	NPC205899
0.8316	Intermediate Similarity	NPC167877
0.8316	Intermediate Similarity	NPC96496
0.8302	Intermediate Similarity	NPC197428
0.8302	Intermediate Similarity	NPC37116
0.83	Intermediate Similarity	NPC190554
0.83	Intermediate Similarity	NPC18319
0.83	Intermediate Similarity	NPC69385
0.8283	Intermediate Similarity	NPC162001
0.8283	Intermediate Similarity	NPC45324
0.8283	Intermediate Similarity	NPC222845
0.8265	Intermediate Similarity	NPC170220
0.8265	Intermediate Similarity	NPC470254
0.8265	Intermediate Similarity	NPC470224
0.8265	Intermediate Similarity	NPC169343
0.8265	Intermediate Similarity	NPC141497
0.8265	Intermediate Similarity	NPC25750
0.8265	Intermediate Similarity	NPC107674
0.8257	Intermediate Similarity	NPC148458
0.8252	Intermediate Similarity	NPC474775
0.8252	Intermediate Similarity	NPC221421
0.8247	Intermediate Similarity	NPC320026
0.8247	Intermediate Similarity	NPC46281
0.8247	Intermediate Similarity	NPC123854
0.8247	Intermediate Similarity	NPC20388
0.8247	Intermediate Similarity	NPC471896
0.8247	Intermediate Similarity	NPC198818
0.8247	Intermediate Similarity	NPC171441
0.8241	Intermediate Similarity	NPC962
0.8241	Intermediate Similarity	NPC250109
0.8235	Intermediate Similarity	NPC310981
0.8229	Intermediate Similarity	NPC247406
0.8229	Intermediate Similarity	NPC48866
0.8224	Intermediate Similarity	NPC214797
0.8224	Intermediate Similarity	NPC231589
0.8224	Intermediate Similarity	NPC118860
0.8218	Intermediate Similarity	NPC48647
0.8218	Intermediate Similarity	NPC186810
0.8218	Intermediate Similarity	NPC10364
0.8218	Intermediate Similarity	NPC222011
0.8218	Intermediate Similarity	NPC477854
0.8211	Intermediate Similarity	NPC155011
0.8211	Intermediate Similarity	NPC195640
0.82	Intermediate Similarity	NPC328371
0.82	Intermediate Similarity	NPC111684
0.82	Intermediate Similarity	NPC125622
0.82	Intermediate Similarity	NPC173272
0.82	Intermediate Similarity	NPC49371
0.82	Intermediate Similarity	NPC58052
0.8191	Intermediate Similarity	NPC109512
0.8191	Intermediate Similarity	NPC165064
0.819	Intermediate Similarity	NPC91034
0.819	Intermediate Similarity	NPC220974
0.819	Intermediate Similarity	NPC44063
0.8182	Intermediate Similarity	NPC7165
0.8182	Intermediate Similarity	NPC159410
0.8182	Intermediate Similarity	NPC184870
0.8182	Intermediate Similarity	NPC470959
0.8182	Intermediate Similarity	NPC239273
0.8182	Intermediate Similarity	NPC476965
0.8182	Intermediate Similarity	NPC303863
0.8182	Intermediate Similarity	NPC476415
0.8173	Intermediate Similarity	NPC472227
0.8173	Intermediate Similarity	NPC473175
0.8173	Intermediate Similarity	NPC472228
0.8173	Intermediate Similarity	NPC255309
0.8165	Intermediate Similarity	NPC473898
0.8163	Intermediate Similarity	NPC110657
0.8163	Intermediate Similarity	NPC107690
0.8163	Intermediate Similarity	NPC86266
0.8163	Intermediate Similarity	NPC212301
0.8163	Intermediate Similarity	NPC297265
0.8163	Intermediate Similarity	NPC45269
0.8155	Intermediate Similarity	NPC22388
0.8148	Intermediate Similarity	NPC71348
0.8148	Intermediate Similarity	NPC170487
0.8148	Intermediate Similarity	NPC126691
0.8148	Intermediate Similarity	NPC476163
0.8144	Intermediate Similarity	NPC475921
0.8144	Intermediate Similarity	NPC474704
0.8144	Intermediate Similarity	NPC2983
0.8142	Intermediate Similarity	NPC269642
0.8137	Intermediate Similarity	NPC51370
0.8137	Intermediate Similarity	NPC15390
0.8137	Intermediate Similarity	NPC477521
0.8137	Intermediate Similarity	NPC287833
0.8137	Intermediate Similarity	NPC167974
0.8131	Intermediate Similarity	NPC473627
0.8125	Intermediate Similarity	NPC142361
0.8125	Intermediate Similarity	NPC474684
0.8119	Intermediate Similarity	NPC253826
0.8119	Intermediate Similarity	NPC76266
0.8119	Intermediate Similarity	NPC121339
0.8113	Intermediate Similarity	NPC189075
0.8113	Intermediate Similarity	NPC275539
0.8108	Intermediate Similarity	NPC311554
0.8108	Intermediate Similarity	NPC257457
0.8105	Intermediate Similarity	NPC471224
0.8105	Intermediate Similarity	NPC323765
0.8105	Intermediate Similarity	NPC470223
0.81	Intermediate Similarity	NPC174948
0.81	Intermediate Similarity	NPC173875
0.81	Intermediate Similarity	NPC469995
0.81	Intermediate Similarity	NPC318282
0.81	Intermediate Similarity	NPC470016
0.81	Intermediate Similarity	NPC317586
0.81	Intermediate Similarity	NPC48330
0.81	Intermediate Similarity	NPC241156
0.81	Intermediate Similarity	NPC472932
0.8095	Intermediate Similarity	NPC96377
0.8095	Intermediate Similarity	NPC28791
0.8095	Intermediate Similarity	NPC295366
0.8091	Intermediate Similarity	NPC190286
0.8091	Intermediate Similarity	NPC49492
0.8091	Intermediate Similarity	NPC266728
0.8085	Intermediate Similarity	NPC470046
0.8085	Intermediate Similarity	NPC170862
0.8085	Intermediate Similarity	NPC470047

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 NPC474327 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1421
0.2-0.3	3917
0.3-0.4	2433
0.4-0.5	696
0.5-0.6	172
0.6-0.7	170
0.7-0.8	143
0.8-0.85	34
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8646	High Similarity	NPD6399	Phase 3
0.8447	Intermediate Similarity	NPD5739	Approved
0.8447	Intermediate Similarity	NPD6402	Approved
0.8447	Intermediate Similarity	NPD7128	Approved
0.8447	Intermediate Similarity	NPD6675	Approved
0.8381	Intermediate Similarity	NPD6373	Approved
0.8381	Intermediate Similarity	NPD6372	Approved
0.83	Intermediate Similarity	NPD6084	Phase 2
0.83	Intermediate Similarity	NPD6083	Phase 2
0.8286	Intermediate Similarity	NPD6899	Approved
0.8286	Intermediate Similarity	NPD7320	Approved
0.8286	Intermediate Similarity	NPD6881	Approved
0.8229	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD6649	Approved
0.8224	Intermediate Similarity	NPD6650	Approved
0.8211	Intermediate Similarity	NPD5330	Approved
0.8211	Intermediate Similarity	NPD7334	Approved
0.8211	Intermediate Similarity	NPD7146	Approved
0.8211	Intermediate Similarity	NPD6684	Approved
0.8211	Intermediate Similarity	NPD7521	Approved
0.8211	Intermediate Similarity	NPD6409	Approved
0.819	Intermediate Similarity	NPD5697	Approved
0.819	Intermediate Similarity	NPD5701	Approved
0.8131	Intermediate Similarity	NPD7102	Approved
0.8131	Intermediate Similarity	NPD6883	Approved
0.8131	Intermediate Similarity	NPD7290	Approved
0.8113	Intermediate Similarity	NPD6011	Approved
0.8056	Intermediate Similarity	NPD8130	Phase 1
0.8056	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD6617	Approved
0.8056	Intermediate Similarity	NPD6869	Approved
0.8056	Intermediate Similarity	NPD6847	Approved
0.8041	Intermediate Similarity	NPD6903	Approved
0.8039	Intermediate Similarity	NPD5696	Approved
0.8037	Intermediate Similarity	NPD6014	Approved
0.8037	Intermediate Similarity	NPD6013	Approved
0.8037	Intermediate Similarity	NPD6012	Approved
0.8	Intermediate Similarity	NPD3665	Phase 1
0.8	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD3666	Approved
0.8	Intermediate Similarity	NPD3133	Approved
0.7982	Intermediate Similarity	NPD8297	Approved
0.7982	Intermediate Similarity	NPD6882	Approved
0.798	Intermediate Similarity	NPD5693	Phase 1
0.7959	Intermediate Similarity	NPD5328	Approved
0.7941	Intermediate Similarity	NPD4755	Approved
0.7921	Intermediate Similarity	NPD5695	Phase 3
0.7864	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD6672	Approved
0.7857	Intermediate Similarity	NPD5737	Approved
0.785	Intermediate Similarity	NPD6412	Phase 2
0.7835	Intermediate Similarity	NPD6098	Approved
0.781	Intermediate Similarity	NPD5211	Phase 2
0.78	Intermediate Similarity	NPD5281	Approved
0.78	Intermediate Similarity	NPD8035	Phase 2
0.78	Intermediate Similarity	NPD8034	Phase 2
0.78	Intermediate Similarity	NPD6079	Approved
0.78	Intermediate Similarity	NPD5284	Approved
0.7789	Intermediate Similarity	NPD3667	Approved
0.7788	Intermediate Similarity	NPD4700	Approved
0.7788	Intermediate Similarity	NPD4696	Approved
0.7788	Intermediate Similarity	NPD5285	Approved
0.7788	Intermediate Similarity	NPD5286	Approved
0.7788	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD7639	Approved
0.7778	Intermediate Similarity	NPD6080	Approved
0.7778	Intermediate Similarity	NPD4753	Phase 2
0.7778	Intermediate Similarity	NPD6904	Approved
0.7778	Intermediate Similarity	NPD6673	Approved
0.7778	Intermediate Similarity	NPD6051	Approved
0.7767	Intermediate Similarity	NPD7902	Approved
0.7757	Intermediate Similarity	NPD6008	Approved
0.7745	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD4202	Approved
0.7714	Intermediate Similarity	NPD5223	Approved
0.7699	Intermediate Similarity	NPD7115	Discovery
0.767	Intermediate Similarity	NPD4697	Phase 3
0.7664	Intermediate Similarity	NPD5141	Approved
0.7658	Intermediate Similarity	NPD6053	Discontinued
0.7653	Intermediate Similarity	NPD3618	Phase 1
0.7647	Intermediate Similarity	NPD7748	Approved
0.7642	Intermediate Similarity	NPD4633	Approved
0.7642	Intermediate Similarity	NPD5226	Approved
0.7642	Intermediate Similarity	NPD5224	Approved
0.7642	Intermediate Similarity	NPD5225	Approved
0.7632	Intermediate Similarity	NPD6335	Approved
0.7627	Intermediate Similarity	NPD7507	Approved
0.7624	Intermediate Similarity	NPD7515	Phase 2
0.7611	Intermediate Similarity	NPD6274	Approved
0.7604	Intermediate Similarity	NPD6435	Approved
0.7604	Intermediate Similarity	NPD4221	Approved
0.7604	Intermediate Similarity	NPD4223	Phase 3
0.7589	Intermediate Similarity	NPD4632	Approved
0.7573	Intermediate Similarity	NPD5210	Approved
0.7573	Intermediate Similarity	NPD4629	Approved
0.757	Intermediate Similarity	NPD5174	Approved
0.757	Intermediate Similarity	NPD5175	Approved
0.757	Intermediate Similarity	NPD4754	Approved
0.7565	Intermediate Similarity	NPD7101	Approved
0.7565	Intermediate Similarity	NPD7100	Approved
0.7551	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5329	Approved
0.7544	Intermediate Similarity	NPD6317	Approved
0.75	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD5221	Approved
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD6314	Approved
0.7478	Intermediate Similarity	NPD6313	Approved
0.7476	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7900	Approved
0.7451	Intermediate Similarity	NPD6050	Approved
0.7451	Intermediate Similarity	NPD6411	Approved
0.7449	Intermediate Similarity	NPD4197	Approved
0.7438	Intermediate Similarity	NPD7319	Approved
0.7436	Intermediate Similarity	NPD6908	Approved
0.7436	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6909	Approved
0.7431	Intermediate Similarity	NPD4768	Approved
0.7431	Intermediate Similarity	NPD4767	Approved
0.7429	Intermediate Similarity	NPD5173	Approved
0.7396	Intermediate Similarity	NPD5368	Approved
0.7391	Intermediate Similarity	NPD6009	Approved
0.7374	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5207	Approved
0.7353	Intermediate Similarity	NPD5692	Phase 3
0.7353	Intermediate Similarity	NPD5785	Approved
0.735	Intermediate Similarity	NPD6319	Approved
0.7347	Intermediate Similarity	NPD4788	Approved
0.7311	Intermediate Similarity	NPD7604	Phase 2
0.7308	Intermediate Similarity	NPD6001	Approved
0.7304	Intermediate Similarity	NPD6868	Approved
0.73	Intermediate Similarity	NPD4693	Phase 3
0.73	Intermediate Similarity	NPD4690	Approved
0.73	Intermediate Similarity	NPD5205	Approved
0.73	Intermediate Similarity	NPD4689	Approved
0.73	Intermediate Similarity	NPD5786	Approved
0.73	Intermediate Similarity	NPD4688	Approved
0.73	Intermediate Similarity	NPD4138	Approved
0.73	Intermediate Similarity	NPD5279	Phase 3
0.7297	Intermediate Similarity	NPD4729	Approved
0.7297	Intermediate Similarity	NPD5128	Approved
0.7297	Intermediate Similarity	NPD4730	Approved
0.7297	Intermediate Similarity	NPD6686	Approved
0.7288	Intermediate Similarity	NPD5983	Phase 2
0.7282	Intermediate Similarity	NPD5694	Approved
0.7273	Intermediate Similarity	NPD3668	Phase 3
0.7255	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6101	Approved
0.725	Intermediate Similarity	NPD7492	Approved
0.7245	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3702	Approved
0.7228	Intermediate Similarity	NPD3573	Approved
0.7213	Intermediate Similarity	NPD7736	Approved
0.7203	Intermediate Similarity	NPD6059	Approved
0.7203	Intermediate Similarity	NPD6054	Approved
0.719	Intermediate Similarity	NPD6336	Discontinued
0.719	Intermediate Similarity	NPD6616	Approved
0.7188	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5362	Discontinued
0.7168	Intermediate Similarity	NPD5248	Approved
0.7168	Intermediate Similarity	NPD5250	Approved
0.7168	Intermediate Similarity	NPD5169	Approved
0.7168	Intermediate Similarity	NPD5251	Approved
0.7168	Intermediate Similarity	NPD5247	Approved
0.7168	Intermediate Similarity	NPD4634	Approved
0.7168	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5249	Phase 3
0.7168	Intermediate Similarity	NPD5135	Approved
0.7158	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD5369	Approved
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD8293	Discontinued
0.7131	Intermediate Similarity	NPD7078	Approved
0.713	Intermediate Similarity	NPD8133	Approved
0.7129	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4694	Approved
0.7129	Intermediate Similarity	NPD5690	Phase 2
0.7129	Intermediate Similarity	NPD5280	Approved
0.7105	Intermediate Similarity	NPD5216	Approved
0.7105	Intermediate Similarity	NPD5215	Approved
0.7105	Intermediate Similarity	NPD5127	Approved
0.7105	Intermediate Similarity	NPD5217	Approved
0.7091	Intermediate Similarity	NPD6052	Approved
0.7083	Intermediate Similarity	NPD6370	Approved
0.7075	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4270	Approved
0.7071	Intermediate Similarity	NPD4269	Approved
0.7053	Intermediate Similarity	NPD7339	Approved
0.7053	Intermediate Similarity	NPD6942	Approved
0.7041	Intermediate Similarity	NPD7525	Registered
0.7034	Intermediate Similarity	NPD7327	Approved
0.7034	Intermediate Similarity	NPD7328	Approved
0.703	Intermediate Similarity	NPD1694	Approved
0.7	Intermediate Similarity	NPD7503	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.6975	Remote Similarity	NPD7516	Approved
0.697	Remote Similarity	NPD4139	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