NPASS Compound

Structure

CID3915 OpenBabel06191715322D 32 36 0 0 1 0 0 0 0 0999 V2000 4.4649 0.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9850 -1.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5008 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0143 0.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5279 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 1 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 2.5279 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3705 -2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 30 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 30 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	6.541
LogD:	4.921
LogS:	-5.791
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	4.668
Fsp3:	0.9
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:	-5.143
MDCK Permeability:	8.589154276705813e-06
Pgp-inhibitor:	0.02
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.825
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	94.98469543457031%
Volume Distribution (VD):	1.124
Pgp-substrate:	2.143965244293213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.378
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.232
CYP2C9-substrate:	0.534
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.306
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.562

ADMET: Excretion

Clearance (CL):	6.529
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.622
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.042
Carcinogencity:	0.23
Eye Corrosion:	0.024
Eye Irritation:	0.134
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC3915

Natural Product ID:	NPC3915
*Common Name:**	3-Oxo-Erythrodiol
IUPAC Name:	(4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1H-picen-3-one
Synonyms:	3-Oxo-Erythrodiol
Standard InCHIKey:	LCZGVWKWRGLAFX-CHMVMOPFSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-25(2)14-16-30(19-31)17-15-28(6)20(21(30)18-25)8-9-23-27(5)12-11-24(32)26(3,4)22(27)10-13-29(23,28)7/h8,21-23,31H,9-19H2,1-7H3/t21-,22-,23+,27-,28+,29+,30+/m0/s1
SMILES:	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631831
PubChem CID:	15127783
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
NPO21797	Derris brevipes	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15081	Aleuroglyphus ovatus	Species	Acaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17642	Chondropetalum paniculatum	Species	Restionaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	1.17	%	PMID[469492]

☑ 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 NPC3915 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	181
0.1-0.2	1299
0.2-0.3	5930
0.3-0.4	16495
0.4-0.5	7524
0.5-0.6	5253
0.6-0.7	4226
0.7-0.8	1326
0.8-0.85	265
0.85-0.9	150
0.9-0.95	43
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC310989
0.9615	High Similarity	NPC180834
0.9494	High Similarity	NPC133954
0.9494	High Similarity	NPC274724
0.9375	High Similarity	NPC74363
0.9375	High Similarity	NPC213412
0.9375	High Similarity	NPC475862
0.9259	High Similarity	NPC158141
0.9259	High Similarity	NPC73064
0.9259	High Similarity	NPC173089
0.9231	High Similarity	NPC274050
0.9231	High Similarity	NPC162632
0.9231	High Similarity	NPC263272
0.9231	High Similarity	NPC267691
0.9146	High Similarity	NPC474511
0.9146	High Similarity	NPC1753
0.9136	High Similarity	NPC95594
0.9136	High Similarity	NPC477579
0.9136	High Similarity	NPC235341
0.9114	High Similarity	NPC251779
0.9114	High Similarity	NPC69101
0.9103	High Similarity	NPC2482
0.9036	High Similarity	NPC281524
0.9036	High Similarity	NPC69627
0.9024	High Similarity	NPC142415
0.9024	High Similarity	NPC18064
0.9024	High Similarity	NPC242468
0.9024	High Similarity	NPC171203
0.9024	High Similarity	NPC98442
0.9024	High Similarity	NPC307426
0.9024	High Similarity	NPC130577
0.9024	High Similarity	NPC102683
0.9024	High Similarity	NPC68160
0.9024	High Similarity	NPC51700
0.9024	High Similarity	NPC88716
0.9024	High Similarity	NPC293564
0.9	High Similarity	NPC70834
0.8974	High Similarity	NPC16394
0.8929	High Similarity	NPC46441
0.8929	High Similarity	NPC193750
0.8929	High Similarity	NPC291028
0.8916	High Similarity	NPC290690
0.8916	High Similarity	NPC473242
0.8916	High Similarity	NPC246708
0.8916	High Similarity	NPC474474
0.8916	High Similarity	NPC470629
0.8916	High Similarity	NPC182797
0.8916	High Similarity	NPC17733
0.8916	High Similarity	NPC40552
0.8916	High Similarity	NPC52169
0.8916	High Similarity	NPC474512
0.8916	High Similarity	NPC181225
0.8902	High Similarity	NPC72638
0.8889	High Similarity	NPC96095
0.8875	High Similarity	NPC163236
0.8861	High Similarity	NPC267517
0.8824	High Similarity	NPC4036
0.8824	High Similarity	NPC158030
0.8824	High Similarity	NPC474525
0.8824	High Similarity	NPC233455
0.8824	High Similarity	NPC65120
0.8824	High Similarity	NPC471588
0.8824	High Similarity	NPC105189
0.8824	High Similarity	NPC38754
0.8824	High Similarity	NPC6255
0.8824	High Similarity	NPC145067
0.881	High Similarity	NPC474700
0.881	High Similarity	NPC234346
0.881	High Similarity	NPC95246
0.881	High Similarity	NPC474972
0.881	High Similarity	NPC293048
0.881	High Similarity	NPC270768
0.881	High Similarity	NPC290972
0.881	High Similarity	NPC61543
0.881	High Similarity	NPC161751
0.881	High Similarity	NPC263393
0.881	High Similarity	NPC130520
0.881	High Similarity	NPC470588
0.881	High Similarity	NPC25906
0.881	High Similarity	NPC59263
0.881	High Similarity	NPC225585
0.881	High Similarity	NPC127689
0.881	High Similarity	NPC143232
0.881	High Similarity	NPC64872
0.881	High Similarity	NPC274330
0.881	High Similarity	NPC198664
0.881	High Similarity	NPC121798
0.8795	High Similarity	NPC93778
0.8795	High Similarity	NPC71507
0.8765	High Similarity	NPC307258
0.8765	High Similarity	NPC53733
0.8765	High Similarity	NPC200752
0.875	High Similarity	NPC121984
0.875	High Similarity	NPC471898
0.8734	High Similarity	NPC474113
0.8734	High Similarity	NPC231431
0.8734	High Similarity	NPC201459
0.8721	High Similarity	NPC272075
0.8721	High Similarity	NPC118490
0.8721	High Similarity	NPC214756
0.8721	High Similarity	NPC295643
0.8718	High Similarity	NPC471897
0.8718	High Similarity	NPC471899
0.8718	High Similarity	NPC107039
0.8706	High Similarity	NPC227467
0.8706	High Similarity	NPC290614
0.8706	High Similarity	NPC126369
0.8706	High Similarity	NPC130278
0.8706	High Similarity	NPC198818
0.8706	High Similarity	NPC86372
0.8706	High Similarity	NPC120968
0.8706	High Similarity	NPC210037
0.8706	High Similarity	NPC273621
0.8706	High Similarity	NPC172361
0.8706	High Similarity	NPC18872
0.8706	High Similarity	NPC470589
0.8706	High Similarity	NPC477872
0.8706	High Similarity	NPC111110
0.8706	High Similarity	NPC7260
0.869	High Similarity	NPC472802
0.8675	High Similarity	NPC324063
0.8675	High Similarity	NPC158393
0.8659	High Similarity	NPC227132
0.8659	High Similarity	NPC85774
0.8659	High Similarity	NPC312660
0.8659	High Similarity	NPC82902
0.8659	High Similarity	NPC59453
0.8659	High Similarity	NPC221758
0.8659	High Similarity	NPC214043
0.8642	High Similarity	NPC212083
0.8642	High Similarity	NPC48362
0.8642	High Similarity	NPC151519
0.8625	High Similarity	NPC18955
0.8625	High Similarity	NPC37038
0.8625	High Similarity	NPC472478
0.8625	High Similarity	NPC104545
0.8621	High Similarity	NPC148964
0.8621	High Similarity	NPC474529
0.8608	High Similarity	NPC260385
0.8608	High Similarity	NPC110094
0.8608	High Similarity	NPC280654
0.8605	High Similarity	NPC288833
0.8605	High Similarity	NPC187722
0.8605	High Similarity	NPC228784
0.8605	High Similarity	NPC235884
0.8605	High Similarity	NPC155120
0.8605	High Similarity	NPC472149
0.8605	High Similarity	NPC324341
0.8605	High Similarity	NPC282616
0.8605	High Similarity	NPC966
0.8605	High Similarity	NPC300351
0.8605	High Similarity	NPC52021
0.8605	High Similarity	NPC84319
0.8605	High Similarity	NPC25299
0.8605	High Similarity	NPC71074
0.8605	High Similarity	NPC306541
0.859	High Similarity	NPC89294
0.8588	High Similarity	NPC184663
0.8588	High Similarity	NPC477973
0.8588	High Similarity	NPC474686
0.8554	High Similarity	NPC469948
0.8554	High Similarity	NPC474218
0.8554	High Similarity	NPC471224
0.8554	High Similarity	NPC474537
0.8554	High Similarity	NPC469993
0.8533	High Similarity	NPC286814
0.8523	High Similarity	NPC139570
0.8523	High Similarity	NPC148523
0.8519	High Similarity	NPC142244
0.8519	High Similarity	NPC474484
0.8519	High Similarity	NPC103754
0.8519	High Similarity	NPC14151
0.8506	High Similarity	NPC307335
0.8506	High Similarity	NPC118519
0.8506	High Similarity	NPC158059
0.8506	High Similarity	NPC275809
0.8506	High Similarity	NPC86368
0.8506	High Similarity	NPC229281
0.8506	High Similarity	NPC74855
0.8506	High Similarity	NPC474436
0.8506	High Similarity	NPC49776
0.8506	High Similarity	NPC298554
0.8506	High Similarity	NPC136313
0.8506	High Similarity	NPC63118
0.8506	High Similarity	NPC169343
0.8506	High Similarity	NPC202728
0.85	High Similarity	NPC199595
0.85	High Similarity	NPC215843
0.8488	Intermediate Similarity	NPC85173
0.8488	Intermediate Similarity	NPC49320
0.8488	Intermediate Similarity	NPC113989
0.8488	Intermediate Similarity	NPC120840
0.8488	Intermediate Similarity	NPC474728
0.8481	Intermediate Similarity	NPC40394
0.8481	Intermediate Similarity	NPC157996
0.8481	Intermediate Similarity	NPC101475
0.8481	Intermediate Similarity	NPC34177
0.8481	Intermediate Similarity	NPC325946
0.8471	Intermediate Similarity	NPC206060
0.8471	Intermediate Similarity	NPC230387

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 NPC3915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1687
0.2-0.3	4083
0.3-0.4	2241
0.4-0.5	551
0.5-0.6	175
0.6-0.7	174
0.7-0.8	63
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD7515	Phase 2
0.8659	High Similarity	NPD4786	Approved
0.8642	High Similarity	NPD3667	Approved
0.8434	Intermediate Similarity	NPD3133	Approved
0.8434	Intermediate Similarity	NPD3665	Phase 1
0.8434	Intermediate Similarity	NPD3666	Approved
0.8409	Intermediate Similarity	NPD7748	Approved
0.8272	Intermediate Similarity	NPD7645	Phase 2
0.8235	Intermediate Similarity	NPD3618	Phase 1
0.8161	Intermediate Similarity	NPD5328	Approved
0.8132	Intermediate Similarity	NPD7902	Approved
0.7978	Intermediate Similarity	NPD6079	Approved
0.7976	Intermediate Similarity	NPD4223	Phase 3
0.7976	Intermediate Similarity	NPD4221	Approved
0.7955	Intermediate Similarity	NPD4753	Phase 2
0.7955	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4695	Discontinued
0.7907	Intermediate Similarity	NPD5329	Approved
0.7907	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4788	Approved
0.7841	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD5279	Phase 3
0.7802	Intermediate Similarity	NPD7900	Approved
0.7802	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4197	Approved
0.7791	Intermediate Similarity	NPD3668	Phase 3
0.7711	Intermediate Similarity	NPD3617	Approved
0.7692	Intermediate Similarity	NPD6399	Phase 3
0.7692	Intermediate Similarity	NPD4202	Approved
0.7614	Intermediate Similarity	NPD5205	Approved
0.7614	Intermediate Similarity	NPD4690	Approved
0.7614	Intermediate Similarity	NPD4688	Approved
0.7614	Intermediate Similarity	NPD4519	Discontinued
0.7614	Intermediate Similarity	NPD7521	Approved
0.7614	Intermediate Similarity	NPD7334	Approved
0.7614	Intermediate Similarity	NPD4623	Approved
0.7614	Intermediate Similarity	NPD6684	Approved
0.7614	Intermediate Similarity	NPD4693	Phase 3
0.7614	Intermediate Similarity	NPD7146	Approved
0.7614	Intermediate Similarity	NPD4138	Approved
0.7614	Intermediate Similarity	NPD6409	Approved
0.7614	Intermediate Similarity	NPD4689	Approved
0.7614	Intermediate Similarity	NPD5330	Approved
0.7561	Intermediate Similarity	NPD6942	Approved
0.7561	Intermediate Similarity	NPD7339	Approved
0.7553	Intermediate Similarity	NPD6083	Phase 2
0.7553	Intermediate Similarity	NPD6084	Phase 2
0.7527	Intermediate Similarity	NPD5210	Approved
0.7527	Intermediate Similarity	NPD4629	Approved
0.747	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5221	Approved
0.7447	Intermediate Similarity	NPD4697	Phase 3
0.7447	Intermediate Similarity	NPD7614	Phase 1
0.7447	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5222	Approved
0.7444	Intermediate Similarity	NPD6903	Approved
0.7444	Intermediate Similarity	NPD5737	Approved
0.7444	Intermediate Similarity	NPD6672	Approved
0.7416	Intermediate Similarity	NPD5690	Phase 2
0.7416	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5280	Approved
0.7416	Intermediate Similarity	NPD4694	Approved
0.7375	Intermediate Similarity	NPD4137	Phase 3
0.7368	Intermediate Similarity	NPD5173	Approved
0.7368	Intermediate Similarity	NPD4755	Approved
0.7326	Intermediate Similarity	NPD7525	Registered
0.7284	Intermediate Similarity	NPD4245	Approved
0.7284	Intermediate Similarity	NPD4244	Approved
0.7284	Intermediate Similarity	NPD4691	Approved
0.7284	Intermediate Similarity	NPD4789	Approved
0.7284	Intermediate Similarity	NPD4747	Approved
0.725	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4692	Approved
0.7241	Intermediate Similarity	NPD4139	Approved
0.7222	Intermediate Similarity	NPD6098	Approved
0.7216	Intermediate Similarity	NPD5286	Approved
0.7216	Intermediate Similarity	NPD5285	Approved
0.7216	Intermediate Similarity	NPD4700	Approved
0.7216	Intermediate Similarity	NPD4696	Approved
0.7209	Intermediate Similarity	NPD4195	Approved
0.7204	Intermediate Similarity	NPD8035	Phase 2
0.7204	Intermediate Similarity	NPD8034	Phase 2
0.7195	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4243	Approved
0.716	Intermediate Similarity	NPD3698	Phase 2
0.716	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD3573	Approved
0.7143	Intermediate Similarity	NPD5223	Approved
0.7129	Intermediate Similarity	NPD6412	Phase 2
0.7113	Intermediate Similarity	NPD5696	Approved
0.7089	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7732	Phase 3
0.7071	Intermediate Similarity	NPD5211	Phase 2
0.7071	Intermediate Similarity	NPD4633	Approved
0.7071	Intermediate Similarity	NPD5224	Approved
0.7071	Intermediate Similarity	NPD5225	Approved
0.7071	Intermediate Similarity	NPD5226	Approved
0.7045	Intermediate Similarity	NPD8028	Phase 2
0.703	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD7128	Approved
0.703	Intermediate Similarity	NPD5739	Approved
0.703	Intermediate Similarity	NPD6675	Approved
0.7024	Intermediate Similarity	NPD4058	Approved
0.7024	Intermediate Similarity	NPD6924	Approved
0.7024	Intermediate Similarity	NPD5733	Approved
0.7024	Intermediate Similarity	NPD4785	Approved
0.7024	Intermediate Similarity	NPD4784	Approved
0.7024	Intermediate Similarity	NPD6926	Approved
0.7021	Intermediate Similarity	NPD5281	Approved
0.7021	Intermediate Similarity	NPD6411	Approved
0.7021	Intermediate Similarity	NPD5284	Approved
0.7	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD5174	Approved
0.7	Intermediate Similarity	NPD5175	Approved
0.7	Intermediate Similarity	NPD7331	Phase 2
0.6989	Remote Similarity	NPD6904	Approved
0.6989	Remote Similarity	NPD6080	Approved
0.6989	Remote Similarity	NPD6673	Approved
0.6939	Remote Similarity	NPD7638	Approved
0.6931	Remote Similarity	NPD5141	Approved
0.6915	Remote Similarity	NPD4096	Approved
0.6893	Remote Similarity	NPD6899	Approved
0.6893	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD7320	Approved
0.6882	Remote Similarity	NPD5208	Approved
0.6875	Remote Similarity	NPD7341	Phase 2
0.6869	Remote Similarity	NPD7640	Approved
0.6869	Remote Similarity	NPD7639	Approved
0.6863	Remote Similarity	NPD4767	Approved
0.6863	Remote Similarity	NPD4768	Approved
0.686	Remote Similarity	NPD6933	Approved
0.6829	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5360	Phase 3
0.6827	Remote Similarity	NPD6373	Approved
0.6827	Remote Similarity	NPD6372	Approved
0.6824	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4687	Approved
0.6809	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6101	Approved
0.6804	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5701	Approved
0.6796	Remote Similarity	NPD5697	Approved
0.679	Remote Similarity	NPD4224	Phase 2
0.6786	Remote Similarity	NPD5276	Approved
0.6778	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5133	Approved
0.6762	Remote Similarity	NPD7290	Approved
0.6762	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6747	Remote Similarity	NPD6922	Approved
0.6747	Remote Similarity	NPD6923	Approved
0.6744	Remote Similarity	NPD3703	Phase 2
0.6744	Remote Similarity	NPD5275	Approved
0.6744	Remote Similarity	NPD4190	Phase 3
0.6742	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5128	Approved
0.6731	Remote Similarity	NPD4730	Approved
0.6731	Remote Similarity	NPD6011	Approved
0.6731	Remote Similarity	NPD5168	Approved
0.6731	Remote Similarity	NPD4729	Approved
0.6705	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4518	Approved
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD6650	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6649	Approved
0.6698	Remote Similarity	NPD8130	Phase 1
0.6698	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD8328	Phase 3
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6629	Remote Similarity	NPD6929	Approved
0.6604	Remote Similarity	NPD5251	Approved
0.6604	Remote Similarity	NPD5250	Approved
0.6604	Remote Similarity	NPD5247	Approved
0.6604	Remote Similarity	NPD5248	Approved
0.6604	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5169	Approved
0.6604	Remote Similarity	NPD5135	Approved
0.6604	Remote Similarity	NPD4634	Approved
0.6604	Remote Similarity	NPD5249	Phase 3
0.6596	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6116	Phase 1
0.6588	Remote Similarity	NPD7152	Approved
0.6588	Remote Similarity	NPD7151	Approved
0.6588	Remote Similarity	NPD7150	Approved
0.6588	Remote Similarity	NPD6081	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