NPASS Compound

Structure

NPC110657 OpenBabel07101718332D 34 37 0 0 1 0 0 0 0 0999 V2000 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 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 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1871 -5.1132 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 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 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 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2308 -4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8270 -6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -5.6485 0.0000 O 0 0 0 0 0 0 0 0 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 9 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 10 21 2 0 0 0 0 11 15 1 0 0 0 0 11 22 2 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 1 1 1 0 0 0 18 21 1 0 0 0 0 19 2 1 6 0 0 0 19 26 1 0 0 0 0 20 31 2 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 6 0 0 0 24 27 1 0 0 0 0 24 28 1 1 0 0 0 25 27 1 0 0 0 0 25 32 1 1 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	517.825
LogP:	5.536
LogD:	3.943
LogS:	-3.551
# 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:	0.43
Synthetic Accessibility Score:	4.957
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:	-5.25
MDCK Permeability:	1.3894525181967765e-05
Pgp-inhibitor:	0.691
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.829
30% Bioavailability (F30%):	0.578

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	89.08876037597656%
Volume Distribution (VD):	0.795
Pgp-substrate:	11.551068305969238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.256
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.374
CYP3A4-substrate:	0.483

ADMET: Excretion

Clearance (CL):	18.533
Half-life (T1/2):	0.101

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.139
Carcinogencity:	0.875
Eye Corrosion:	0.012
Eye Irritation:	0.014
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC110657

Natural Product ID:	NPC110657
*Common Name:**	Garcihombronanes D
IUPAC Name:	(2R,6R)-6-[(3S,5R,8S,10S,13S,14S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,12,15-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid
Synonyms:	Garcihombronanes D
Standard InCHIKey:	MSMIBGMKDUWCSX-HZAMRZAGSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18(16-20(31)17-19(2)26(33)34)21-10-14-30(7)23-8-9-24-27(3,4)25(32)12-13-28(24,5)22(23)11-15-29(21,30)6/h10-11,18-19,23-25,32H,8-9,12-17H2,1-7H3,(H,33,34)/t18-,19-,23-,24+,25+,28-,29-,30+/m1/s1
SMILES:	O=C(C[C@H](C1=CC[C@@]2([C@]1(C)CC=C1[C@H]2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C)C[C@H](C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469624
PubChem CID:	44559191
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
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[542226]

☑ 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 NPC110657 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	183
0.1-0.2	1132
0.2-0.3	4648
0.3-0.4	13550
0.4-0.5	9173
0.5-0.6	6155
0.6-0.7	4742
0.7-0.8	2614
0.8-0.85	448
0.85-0.9	41
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC212301
1.0	High Similarity	NPC86266
0.9884	High Similarity	NPC170220
0.9884	High Similarity	NPC141497
0.9884	High Similarity	NPC107674
0.977	High Similarity	NPC49670
0.9545	High Similarity	NPC159410
0.9318	High Similarity	NPC297265
0.931	High Similarity	NPC475921
0.931	High Similarity	NPC474704
0.9302	High Similarity	NPC142361
0.9302	High Similarity	NPC474684
0.9213	High Similarity	NPC470376
0.9213	High Similarity	NPC470375
0.9101	High Similarity	NPC189520
0.908	High Similarity	NPC187376
0.908	High Similarity	NPC233836
0.908	High Similarity	NPC159046
0.9	High Similarity	NPC470224
0.8989	High Similarity	NPC471896
0.8989	High Similarity	NPC291028
0.8977	High Similarity	NPC242864
0.8966	High Similarity	NPC73038
0.8966	High Similarity	NPC155011
0.8966	High Similarity	NPC28252
0.8966	High Similarity	NPC55309
0.8889	High Similarity	NPC154101
0.8889	High Similarity	NPC105189
0.8889	High Similarity	NPC23434
0.8876	High Similarity	NPC119416
0.8876	High Similarity	NPC84271
0.8876	High Similarity	NPC77168
0.8876	High Similarity	NPC102414
0.8864	High Similarity	NPC96496
0.8817	High Similarity	NPC108078
0.8804	High Similarity	NPC45324
0.8804	High Similarity	NPC222845
0.8804	High Similarity	NPC469599
0.8804	High Similarity	NPC139459
0.8804	High Similarity	NPC162001
0.8778	High Similarity	NPC148414
0.8778	High Similarity	NPC175628
0.8778	High Similarity	NPC7260
0.8778	High Similarity	NPC469400
0.8778	High Similarity	NPC227467
0.8778	High Similarity	NPC290614
0.8778	High Similarity	NPC18872
0.8778	High Similarity	NPC111585
0.8778	High Similarity	NPC273621
0.8778	High Similarity	NPC193750
0.8778	High Similarity	NPC477872
0.8778	High Similarity	NPC85173
0.8778	High Similarity	NPC210037
0.8778	High Similarity	NPC120968
0.8764	High Similarity	NPC52169
0.8764	High Similarity	NPC182797
0.8764	High Similarity	NPC474719
0.875	High Similarity	NPC325594
0.8736	High Similarity	NPC221758
0.8736	High Similarity	NPC59453
0.8723	High Similarity	NPC194196
0.8721	High Similarity	NPC133391
0.871	High Similarity	NPC235053
0.8696	High Similarity	NPC469406
0.8696	High Similarity	NPC166906
0.8681	High Similarity	NPC26888
0.8681	High Similarity	NPC158030
0.8681	High Similarity	NPC187722
0.8681	High Similarity	NPC38754
0.8681	High Similarity	NPC474525
0.8681	High Similarity	NPC4036
0.8681	High Similarity	NPC233455
0.8681	High Similarity	NPC65120
0.8681	High Similarity	NPC145067
0.8667	High Similarity	NPC130520
0.8667	High Similarity	NPC31985
0.8667	High Similarity	NPC61543
0.8667	High Similarity	NPC1015
0.8667	High Similarity	NPC474245
0.8667	High Similarity	NPC270768
0.8667	High Similarity	NPC121798
0.8667	High Similarity	NPC263393
0.8667	High Similarity	NPC225585
0.8667	High Similarity	NPC290972
0.8667	High Similarity	NPC474889
0.8667	High Similarity	NPC127689
0.8667	High Similarity	NPC54689
0.8667	High Similarity	NPC128496
0.8667	High Similarity	NPC274330
0.8667	High Similarity	NPC293048
0.8667	High Similarity	NPC59263
0.8667	High Similarity	NPC234346
0.8667	High Similarity	NPC25906
0.8667	High Similarity	NPC32830
0.8667	High Similarity	NPC143232
0.8667	High Similarity	NPC64872
0.8667	High Similarity	NPC198664
0.8652	High Similarity	NPC475740
0.8652	High Similarity	NPC130577
0.8652	High Similarity	NPC18064
0.8652	High Similarity	NPC88716
0.8652	High Similarity	NPC51700
0.8652	High Similarity	NPC98442
0.8652	High Similarity	NPC171203
0.8652	High Similarity	NPC102683
0.8652	High Similarity	NPC142415
0.8652	High Similarity	NPC477926
0.8652	High Similarity	NPC293564
0.8652	High Similarity	NPC68160
0.8652	High Similarity	NPC307426
0.8652	High Similarity	NPC242468
0.8646	High Similarity	NPC234892
0.8636	High Similarity	NPC470574
0.8636	High Similarity	NPC474218
0.8605	High Similarity	NPC473420
0.8605	High Similarity	NPC147066
0.8602	High Similarity	NPC184848
0.8602	High Similarity	NPC470016
0.8602	High Similarity	NPC317586
0.8602	High Similarity	NPC69548
0.8602	High Similarity	NPC279974
0.8602	High Similarity	NPC255809
0.8587	High Similarity	NPC295643
0.8587	High Similarity	NPC272075
0.8587	High Similarity	NPC66429
0.8587	High Similarity	NPC118519
0.8587	High Similarity	NPC118490
0.8587	High Similarity	NPC158059
0.8587	High Similarity	NPC229281
0.8587	High Similarity	NPC152897
0.8587	High Similarity	NPC477855
0.8587	High Similarity	NPC214756
0.8587	High Similarity	NPC474436
0.8587	High Similarity	NPC49776
0.8587	High Similarity	NPC63118
0.8587	High Similarity	NPC475255
0.8587	High Similarity	NPC202728
0.8571	High Similarity	NPC130278
0.8571	High Similarity	NPC46441
0.8571	High Similarity	NPC126369
0.8571	High Similarity	NPC126993
0.8571	High Similarity	NPC111110
0.8571	High Similarity	NPC470589
0.8556	High Similarity	NPC471722
0.8556	High Similarity	NPC40552
0.8556	High Similarity	NPC181225
0.8556	High Similarity	NPC193360
0.8556	High Similarity	NPC328539
0.8556	High Similarity	NPC470629
0.8556	High Similarity	NPC290690
0.8556	High Similarity	NPC473242
0.8556	High Similarity	NPC17733
0.8556	High Similarity	NPC246708
0.8556	High Similarity	NPC474677
0.8556	High Similarity	NPC474512
0.8539	High Similarity	NPC474733
0.8539	High Similarity	NPC31564
0.8539	High Similarity	NPC475862
0.8539	High Similarity	NPC145879
0.8539	High Similarity	NPC72133
0.8539	High Similarity	NPC474732
0.8539	High Similarity	NPC2783
0.8539	High Similarity	NPC322159
0.8539	High Similarity	NPC474778
0.8539	High Similarity	NPC74363
0.8539	High Similarity	NPC72638
0.8539	High Similarity	NPC474970
0.8539	High Similarity	NPC51014
0.8539	High Similarity	NPC94755
0.8526	High Similarity	NPC114274
0.8526	High Similarity	NPC48647
0.8526	High Similarity	NPC477813
0.8526	High Similarity	NPC186810
0.8523	High Similarity	NPC82902
0.8523	High Similarity	NPC85774
0.8523	High Similarity	NPC214043
0.8523	High Similarity	NPC165064
0.8511	High Similarity	NPC173272
0.8511	High Similarity	NPC167193
0.8511	High Similarity	NPC157113
0.8511	High Similarity	NPC95565
0.8511	High Similarity	NPC192428
0.8511	High Similarity	NPC62516
0.8511	High Similarity	NPC305483
0.8511	High Similarity	NPC96859
0.8511	High Similarity	NPC472806
0.8511	High Similarity	NPC328162
0.8506	High Similarity	NPC151519
0.8506	High Similarity	NPC48362
0.8495	Intermediate Similarity	NPC191412
0.8495	Intermediate Similarity	NPC474529
0.8495	Intermediate Similarity	NPC114159
0.8495	Intermediate Similarity	NPC196485
0.8495	Intermediate Similarity	NPC6818
0.8495	Intermediate Similarity	NPC111015
0.8495	Intermediate Similarity	NPC245972
0.8478	Intermediate Similarity	NPC185936
0.8478	Intermediate Similarity	NPC71074
0.8478	Intermediate Similarity	NPC306541
0.8478	Intermediate Similarity	NPC272746

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 NPC110657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1501
0.2-0.3	3842
0.3-0.4	2429
0.4-0.5	723
0.5-0.6	194
0.6-0.7	149
0.7-0.8	140
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD6399	Phase 3
0.875	High Similarity	NPD3618	Phase 1
0.8736	High Similarity	NPD4786	Approved
0.8681	High Similarity	NPD7515	Phase 2
0.8667	High Similarity	NPD5328	Approved
0.8511	High Similarity	NPD4697	Phase 3
0.8506	High Similarity	NPD3667	Approved
0.8478	Intermediate Similarity	NPD6079	Approved
0.8427	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD7902	Approved
0.8317	Intermediate Similarity	NPD6372	Approved
0.8317	Intermediate Similarity	NPD6373	Approved
0.8298	Intermediate Similarity	NPD7748	Approved
0.828	Intermediate Similarity	NPD8035	Phase 2
0.828	Intermediate Similarity	NPD8034	Phase 2
0.82	Intermediate Similarity	NPD5739	Approved
0.82	Intermediate Similarity	NPD6675	Approved
0.82	Intermediate Similarity	NPD6402	Approved
0.82	Intermediate Similarity	NPD7128	Approved
0.8191	Intermediate Similarity	NPD4202	Approved
0.8155	Intermediate Similarity	NPD6649	Approved
0.8155	Intermediate Similarity	NPD6650	Approved
0.8125	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5221	Approved
0.8125	Intermediate Similarity	NPD5222	Approved
0.8111	Intermediate Similarity	NPD3133	Approved
0.8111	Intermediate Similarity	NPD3666	Approved
0.8111	Intermediate Similarity	NPD3665	Phase 1
0.8105	Intermediate Similarity	NPD7900	Approved
0.8105	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD6083	Phase 2
0.8041	Intermediate Similarity	NPD5173	Approved
0.8041	Intermediate Similarity	NPD4755	Approved
0.8041	Intermediate Similarity	NPD6084	Phase 2
0.8039	Intermediate Similarity	NPD7320	Approved
0.8039	Intermediate Similarity	NPD6899	Approved
0.8039	Intermediate Similarity	NPD6881	Approved
0.7957	Intermediate Similarity	NPD6672	Approved
0.7957	Intermediate Similarity	NPD5737	Approved
0.7941	Intermediate Similarity	NPD5697	Approved
0.7941	Intermediate Similarity	NPD5701	Approved
0.7935	Intermediate Similarity	NPD6684	Approved
0.7935	Intermediate Similarity	NPD7146	Approved
0.7935	Intermediate Similarity	NPD7521	Approved
0.7935	Intermediate Similarity	NPD7334	Approved
0.7935	Intermediate Similarity	NPD6409	Approved
0.7935	Intermediate Similarity	NPD5330	Approved
0.7912	Intermediate Similarity	NPD3668	Phase 3
0.7885	Intermediate Similarity	NPD7102	Approved
0.7885	Intermediate Similarity	NPD7290	Approved
0.7885	Intermediate Similarity	NPD6883	Approved
0.7879	Intermediate Similarity	NPD5286	Approved
0.7879	Intermediate Similarity	NPD5285	Approved
0.7879	Intermediate Similarity	NPD4700	Approved
0.7879	Intermediate Similarity	NPD4696	Approved
0.7872	Intermediate Similarity	NPD4753	Phase 2
0.7865	Intermediate Similarity	NPD7525	Registered
0.7864	Intermediate Similarity	NPD6011	Approved
0.7835	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6117	Approved
0.781	Intermediate Similarity	NPD6617	Approved
0.781	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6869	Approved
0.781	Intermediate Similarity	NPD8130	Phase 1
0.781	Intermediate Similarity	NPD6847	Approved
0.78	Intermediate Similarity	NPD5223	Approved
0.7788	Intermediate Similarity	NPD6014	Approved
0.7788	Intermediate Similarity	NPD6013	Approved
0.7788	Intermediate Similarity	NPD6012	Approved
0.7778	Intermediate Similarity	NPD5696	Approved
0.7778	Intermediate Similarity	NPD7638	Approved
0.7766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6903	Approved
0.7742	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5279	Phase 3
0.7736	Intermediate Similarity	NPD6882	Approved
0.7736	Intermediate Similarity	NPD8297	Approved
0.7727	Intermediate Similarity	NPD6116	Phase 1
0.7723	Intermediate Similarity	NPD5224	Approved
0.7723	Intermediate Similarity	NPD5211	Phase 2
0.7723	Intermediate Similarity	NPD4633	Approved
0.7723	Intermediate Similarity	NPD5226	Approved
0.7723	Intermediate Similarity	NPD5225	Approved
0.7708	Intermediate Similarity	NPD5284	Approved
0.7708	Intermediate Similarity	NPD5281	Approved
0.7701	Intermediate Similarity	NPD6942	Approved
0.7701	Intermediate Similarity	NPD7339	Approved
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7692	Intermediate Similarity	NPD4223	Phase 3
0.7692	Intermediate Similarity	NPD4221	Approved
0.7653	Intermediate Similarity	NPD5210	Approved
0.7653	Intermediate Similarity	NPD4629	Approved
0.7653	Intermediate Similarity	NPD5695	Phase 3
0.7647	Intermediate Similarity	NPD5174	Approved
0.7647	Intermediate Similarity	NPD4754	Approved
0.7647	Intermediate Similarity	NPD5175	Approved
0.764	Intermediate Similarity	NPD6118	Approved
0.764	Intermediate Similarity	NPD6115	Approved
0.764	Intermediate Similarity	NPD6114	Approved
0.764	Intermediate Similarity	NPD6697	Approved
0.7634	Intermediate Similarity	NPD5329	Approved
0.7615	Intermediate Similarity	NPD7115	Discovery
0.7586	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5141	Approved
0.7553	Intermediate Similarity	NPD6098	Approved
0.7527	Intermediate Similarity	NPD4197	Approved
0.7523	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.75	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD4767	Approved
0.7444	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4788	Approved
0.7416	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6335	Approved
0.7374	Intermediate Similarity	NPD6001	Approved
0.7368	Intermediate Similarity	NPD4690	Approved
0.7368	Intermediate Similarity	NPD5205	Approved
0.7368	Intermediate Similarity	NPD4693	Phase 3
0.7368	Intermediate Similarity	NPD4689	Approved
0.7368	Intermediate Similarity	NPD4138	Approved
0.7368	Intermediate Similarity	NPD4688	Approved
0.7364	Intermediate Similarity	NPD6274	Approved
0.7363	Intermediate Similarity	NPD7645	Phase 2
0.7358	Intermediate Similarity	NPD5128	Approved
0.7358	Intermediate Similarity	NPD5168	Approved
0.7358	Intermediate Similarity	NPD4730	Approved
0.7358	Intermediate Similarity	NPD4729	Approved
0.7356	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6411	Approved
0.7321	Intermediate Similarity	NPD7100	Approved
0.7321	Intermediate Similarity	NPD7101	Approved
0.732	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6317	Approved
0.7297	Intermediate Similarity	NPD6009	Approved
0.7292	Intermediate Similarity	NPD3573	Approved
0.729	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4695	Discontinued
0.7253	Intermediate Similarity	NPD3617	Approved
0.7232	Intermediate Similarity	NPD6314	Approved
0.7232	Intermediate Similarity	NPD6313	Approved
0.7222	Intermediate Similarity	NPD4634	Approved
0.7222	Intermediate Similarity	NPD5250	Approved
0.7222	Intermediate Similarity	NPD5248	Approved
0.7222	Intermediate Similarity	NPD5169	Approved
0.7222	Intermediate Similarity	NPD5247	Approved
0.7222	Intermediate Similarity	NPD5249	Phase 3
0.7222	Intermediate Similarity	NPD5251	Approved
0.7222	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5135	Approved
0.7216	Intermediate Similarity	NPD5208	Approved
0.7193	Intermediate Similarity	NPD6909	Approved
0.7193	Intermediate Similarity	NPD6908	Approved
0.7193	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4623	Approved
0.7188	Intermediate Similarity	NPD4694	Approved
0.7188	Intermediate Similarity	NPD4519	Discontinued
0.7188	Intermediate Similarity	NPD5690	Phase 2
0.7188	Intermediate Similarity	NPD5280	Approved
0.7172	Intermediate Similarity	NPD6050	Approved
0.7172	Intermediate Similarity	NPD5693	Phase 1
0.7156	Intermediate Similarity	NPD5216	Approved
0.7156	Intermediate Similarity	NPD5217	Approved
0.7156	Intermediate Similarity	NPD5215	Approved
0.7156	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6319	Approved
0.7103	Intermediate Similarity	NPD6412	Phase 2
0.7087	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD1694	Approved
0.7071	Intermediate Similarity	NPD5207	Approved
0.7071	Intermediate Similarity	NPD5692	Phase 3
0.7069	Intermediate Similarity	NPD7604	Phase 2
0.7053	Intermediate Similarity	NPD5362	Discontinued
0.7048	Intermediate Similarity	NPD7632	Discontinued
0.7045	Intermediate Similarity	NPD4747	Approved
0.7043	Intermediate Similarity	NPD5983	Phase 2
0.7021	Intermediate Similarity	NPD4139	Approved
0.7021	Intermediate Similarity	NPD4692	Approved
0.7021	Intermediate Similarity	NPD5369	Approved
0.7009	Intermediate Similarity	NPD7492	Approved
0.7	Intermediate Similarity	NPD5694	Approved
0.7	Intermediate Similarity	NPD6924	Approved
0.7	Intermediate Similarity	NPD6926	Approved
0.6989	Remote Similarity	NPD4195	Approved
0.697	Remote Similarity	NPD6051	Approved
0.6966	Remote Similarity	NPD6081	Approved
0.6966	Remote Similarity	NPD4243	Approved
0.6964	Remote Similarity	NPD5167	Approved
0.6957	Remote Similarity	NPD6054	Approved
0.6957	Remote Similarity	NPD6059	Approved
0.6949	Remote Similarity	NPD6336	Discontinued

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