NPASS Compound

Structure

NPC132824 OpenBabel07101718292D 36 40 0 0 1 0 0 0 0 0999 V2000 -5.0694 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5103 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8674 -0.8449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -2.4390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0225 -0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 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 2.5347 -1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3796 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3796 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9981 -0.6185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 0.2264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8918 -0.8449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 3 26 1 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 27 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 6 0 0 0 18 22 1 0 0 0 0 18 26 1 0 0 0 0 19 25 1 1 0 0 0 19 27 1 0 0 0 0 20 25 1 1 0 0 0 20 28 1 0 0 0 0 21 28 1 6 0 0 0 21 31 1 0 0 0 0 22 29 1 6 0 0 0 22 30 1 0 0 0 0 23 28 1 0 0 0 0 23 32 2 0 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 25 2 1 1 0 0 0 26 27 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 6 0 0 0 29 6 1 1 0 0 0 29 36 1 0 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.33
Volume:	529.486
LogP:	3.583
LogD:	2.796
LogS:	-3.57
# Rotatable Bonds:	2
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.383
Synthetic Accessibility Score:	5.031
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.778
MDCK Permeability:	9.23273000807967e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.649

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.335
Plasma Protein Binding (PPB):	91.6939468383789%
Volume Distribution (VD):	0.491
Pgp-substrate:	7.404592037200928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.697
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.291
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.094
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	1.285
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.226
Carcinogencity:	0.027
Eye Corrosion:	0.519
Eye Irritation:	0.501
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC132824

Natural Product ID:	NPC132824
*Common Name:**	Diospyric Acid B
IUPAC Name:	(3R,4R,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-3,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
Synonyms:	diospyric acid B
Standard InCHIKey:	UIEGOKVPCRANSU-NASGHRROSA-N
Standard InCHI:	InChI=1S/C30H46O6/c1-17-9-14-30(24(34)35)16-15-26(3)18(22(30)29(17,6)36)7-8-19-25(2)12-11-21(31)28(5,23(32)33)20(25)10-13-27(19,26)4/h7,17,19-22,31,36H,8-16H2,1-6H3,(H,32,33)(H,34,35)/t17-,19-,20-,21-,22-,25-,26-,27-,28-,29-,30+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H]([C@@](C)([C@@H]5CC[C@@]34C)C(=O)O)O)[C@@H]2[C@]1(C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492457
PubChem CID:	13857523
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
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18798681]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[3430165]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]

☑ 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
IC50	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	IC50	>	30000.0	nM	PMID[523986]

☑ 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 NPC132824 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	221
0.1-0.2	1424
0.2-0.3	4776
0.3-0.4	11846
0.4-0.5	10657
0.5-0.6	5942
0.6-0.7	4906
0.7-0.8	2350
0.8-0.85	275
0.85-0.9	134
0.9-0.95	138
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC174663
0.9775	High Similarity	NPC191412
0.9775	High Similarity	NPC114159
0.9775	High Similarity	NPC6818
0.9674	High Similarity	NPC35239
0.967	High Similarity	NPC187933
0.9663	High Similarity	NPC229281
0.9663	High Similarity	NPC158059
0.9663	High Similarity	NPC202728
0.9663	High Similarity	NPC118519
0.9565	High Similarity	NPC111214
0.9565	High Similarity	NPC271614
0.9565	High Similarity	NPC29765
0.956	High Similarity	NPC116457
0.9556	High Similarity	NPC148964
0.9551	High Similarity	NPC228784
0.9551	High Similarity	NPC288833
0.9551	High Similarity	NPC282616
0.9551	High Similarity	NPC155120
0.9551	High Similarity	NPC324341
0.9551	High Similarity	NPC187722
0.9551	High Similarity	NPC966
0.9457	High Similarity	NPC106112
0.9457	High Similarity	NPC261935
0.9457	High Similarity	NPC9613
0.9457	High Similarity	NPC247139
0.9444	High Similarity	NPC118490
0.9438	High Similarity	NPC290614
0.9438	High Similarity	NPC130278
0.9438	High Similarity	NPC111110
0.9438	High Similarity	NPC86372
0.9438	High Similarity	NPC120968
0.9438	High Similarity	NPC470589
0.9438	High Similarity	NPC126369
0.9438	High Similarity	NPC227467
0.9438	High Similarity	NPC210037
0.9438	High Similarity	NPC172361
0.9438	High Similarity	NPC477872
0.9438	High Similarity	NPC18872
0.9438	High Similarity	NPC7260
0.9438	High Similarity	NPC273621
0.9355	High Similarity	NPC164349
0.9348	High Similarity	NPC173744
0.9348	High Similarity	NPC207922
0.9348	High Similarity	NPC204961
0.9348	High Similarity	NPC259733
0.9348	High Similarity	NPC327179
0.9348	High Similarity	NPC201657
0.9348	High Similarity	NPC158371
0.9348	High Similarity	NPC73004
0.9348	High Similarity	NPC62516
0.9348	High Similarity	NPC157113
0.9341	High Similarity	NPC209868
0.9341	High Similarity	NPC222047
0.9333	High Similarity	NPC105189
0.9333	High Similarity	NPC6255
0.9333	High Similarity	NPC38754
0.9333	High Similarity	NPC471588
0.9326	High Similarity	NPC127689
0.9326	High Similarity	NPC25906
0.9326	High Similarity	NPC234346
0.9326	High Similarity	NPC274330
0.9326	High Similarity	NPC64872
0.9326	High Similarity	NPC198664
0.9326	High Similarity	NPC290972
0.9326	High Similarity	NPC121798
0.9326	High Similarity	NPC263393
0.9326	High Similarity	NPC143232
0.9326	High Similarity	NPC59263
0.9326	High Similarity	NPC61543
0.9326	High Similarity	NPC225585
0.9326	High Similarity	NPC130520
0.9326	High Similarity	NPC293048
0.9326	High Similarity	NPC270768
0.9247	High Similarity	NPC255589
0.9247	High Similarity	NPC259788
0.9239	High Similarity	NPC96916
0.9239	High Similarity	NPC83693
0.9239	High Similarity	NPC195715
0.9239	High Similarity	NPC148523
0.9231	High Similarity	NPC298554
0.9222	High Similarity	NPC291028
0.9222	High Similarity	NPC193750
0.9213	High Similarity	NPC17733
0.9213	High Similarity	NPC182797
0.9213	High Similarity	NPC473242
0.9213	High Similarity	NPC52169
0.9213	High Similarity	NPC474512
0.9213	High Similarity	NPC470629
0.9213	High Similarity	NPC290690
0.9213	High Similarity	NPC181225
0.9158	High Similarity	NPC256247
0.9158	High Similarity	NPC118964
0.914	High Similarity	NPC476327
0.914	High Similarity	NPC98874
0.914	High Similarity	NPC476318
0.913	High Similarity	NPC32407
0.913	High Similarity	NPC231063
0.913	High Similarity	NPC145667
0.913	High Similarity	NPC299996
0.913	High Similarity	NPC88116
0.913	High Similarity	NPC78580
0.913	High Similarity	NPC282395
0.913	High Similarity	NPC23621
0.913	High Similarity	NPC60692
0.913	High Similarity	NPC159365
0.913	High Similarity	NPC474529
0.913	High Similarity	NPC20235
0.913	High Similarity	NPC263548
0.913	High Similarity	NPC184006
0.9121	High Similarity	NPC235704
0.9111	High Similarity	NPC470588
0.9101	High Similarity	NPC102683
0.9101	High Similarity	NPC88716
0.9101	High Similarity	NPC51700
0.9101	High Similarity	NPC130577
0.9101	High Similarity	NPC18064
0.9101	High Similarity	NPC242468
0.9101	High Similarity	NPC171203
0.9101	High Similarity	NPC98442
0.9101	High Similarity	NPC68160
0.9101	High Similarity	NPC293564
0.9101	High Similarity	NPC307426
0.9101	High Similarity	NPC142415
0.9072	High Similarity	NPC284865
0.9043	High Similarity	NPC43686
0.9032	High Similarity	NPC290481
0.9032	High Similarity	NPC23241
0.9032	High Similarity	NPC473240
0.9032	High Similarity	NPC32118
0.9022	High Similarity	NPC275809
0.9022	High Similarity	NPC86368
0.9011	High Similarity	NPC474728
0.9	High Similarity	NPC246708
0.9	High Similarity	NPC40552
0.9	High Similarity	NPC1753
0.9	High Similarity	NPC474511
0.8989	High Similarity	NPC72638
0.8958	High Similarity	NPC54909
0.8958	High Similarity	NPC233012
0.8947	High Similarity	NPC188833
0.8936	High Similarity	NPC167193
0.8936	High Similarity	NPC19376
0.8936	High Similarity	NPC305464
0.8936	High Similarity	NPC25848
0.8936	High Similarity	NPC307282
0.8936	High Similarity	NPC472806
0.8925	High Similarity	NPC80365
0.8913	High Similarity	NPC158030
0.8913	High Similarity	NPC71074
0.8913	High Similarity	NPC285184
0.8913	High Similarity	NPC233455
0.8913	High Similarity	NPC25299
0.8913	High Similarity	NPC475708
0.8913	High Similarity	NPC300351
0.8913	High Similarity	NPC77099
0.8913	High Similarity	NPC52021
0.8913	High Similarity	NPC65120
0.8913	High Similarity	NPC84319
0.8913	High Similarity	NPC306541
0.8913	High Similarity	NPC472149
0.8913	High Similarity	NPC235884
0.8913	High Similarity	NPC4036
0.8913	High Similarity	NPC474525
0.8913	High Similarity	NPC145067
0.8913	High Similarity	NPC60755
0.8913	High Similarity	NPC470590
0.8901	High Similarity	NPC95246
0.8901	High Similarity	NPC474972
0.8901	High Similarity	NPC474686
0.8901	High Similarity	NPC161751
0.8889	High Similarity	NPC71507
0.8889	High Similarity	NPC73064
0.8889	High Similarity	NPC158141
0.8889	High Similarity	NPC173089
0.8842	High Similarity	NPC89225
0.8842	High Similarity	NPC21728
0.8842	High Similarity	NPC312075
0.8842	High Similarity	NPC189880
0.8842	High Similarity	NPC203343
0.8842	High Similarity	NPC26413
0.883	High Similarity	NPC139570
0.8817	High Similarity	NPC474806
0.8817	High Similarity	NPC49776
0.8817	High Similarity	NPC474436
0.8817	High Similarity	NPC214756
0.8817	High Similarity	NPC74855
0.8817	High Similarity	NPC63118
0.8817	High Similarity	NPC272075
0.8817	High Similarity	NPC295643
0.8817	High Similarity	NPC133579
0.8817	High Similarity	NPC307335
0.8817	High Similarity	NPC136313
0.8804	High Similarity	NPC46441
0.8804	High Similarity	NPC120840
0.8804	High Similarity	NPC49320
0.8804	High Similarity	NPC113989
0.8778	High Similarity	NPC73038
0.8778	High Similarity	NPC74363
0.8778	High Similarity	NPC213412

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 NPC132824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1742
0.2-0.3	3784
0.3-0.4	2229
0.4-0.5	742
0.5-0.6	213
0.6-0.7	187
0.7-0.8	49
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8913	High Similarity	NPD7515	Phase 2
0.8646	High Similarity	NPD7902	Approved
0.8526	High Similarity	NPD7748	Approved
0.8333	Intermediate Similarity	NPD7900	Approved
0.8333	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD7645	Phase 2
0.7938	Intermediate Similarity	NPD8035	Phase 2
0.7938	Intermediate Similarity	NPD8034	Phase 2
0.7789	Intermediate Similarity	NPD3618	Phase 1
0.7766	Intermediate Similarity	NPD4786	Approved
0.7755	Intermediate Similarity	NPD6411	Approved
0.7742	Intermediate Similarity	NPD3667	Approved
0.7714	Intermediate Similarity	NPD5739	Approved
0.7714	Intermediate Similarity	NPD7128	Approved
0.7714	Intermediate Similarity	NPD6675	Approved
0.7714	Intermediate Similarity	NPD6402	Approved
0.7664	Intermediate Similarity	NPD6372	Approved
0.7664	Intermediate Similarity	NPD6373	Approved
0.7658	Intermediate Similarity	NPD7115	Discovery
0.7658	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.757	Intermediate Similarity	NPD7320	Approved
0.7565	Intermediate Similarity	NPD8328	Phase 3
0.7551	Intermediate Similarity	NPD5328	Approved
0.7551	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6101	Approved
0.7549	Intermediate Similarity	NPD4755	Approved
0.7527	Intermediate Similarity	NPD7525	Registered
0.7523	Intermediate Similarity	NPD6650	Approved
0.7523	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.7477	Intermediate Similarity	NPD5701	Approved
0.7477	Intermediate Similarity	NPD5697	Approved
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD7102	Approved
0.7423	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4700	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD5285	Approved
0.74	Intermediate Similarity	NPD6079	Approved
0.7379	Intermediate Similarity	NPD6084	Phase 2
0.7379	Intermediate Similarity	NPD6083	Phase 2
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6617	Approved
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6012	Approved
0.7308	Intermediate Similarity	NPD4225	Approved
0.7308	Intermediate Similarity	NPD7638	Approved
0.7297	Intermediate Similarity	NPD6882	Approved
0.7297	Intermediate Similarity	NPD8297	Approved
0.7282	Intermediate Similarity	NPD4697	Phase 3
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5225	Approved
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5211	Phase 2
0.7248	Intermediate Similarity	NPD6011	Approved
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7216	Intermediate Similarity	NPD3665	Phase 1
0.7216	Intermediate Similarity	NPD3666	Approved
0.7216	Intermediate Similarity	NPD3668	Phase 3
0.7216	Intermediate Similarity	NPD3133	Approved
0.7207	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6116	Phase 1
0.72	Intermediate Similarity	NPD4753	Phase 2
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7172	Intermediate Similarity	NPD3573	Approved
0.717	Intermediate Similarity	NPD5223	Approved
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD5696	Approved
0.713	Intermediate Similarity	NPD5141	Approved
0.7117	Intermediate Similarity	NPD4634	Approved
0.7115	Intermediate Similarity	NPD5222	Approved
0.7115	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5221	Approved
0.7097	Intermediate Similarity	NPD6117	Approved
0.7091	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7064	Intermediate Similarity	NPD4767	Approved
0.7064	Intermediate Similarity	NPD6008	Approved
0.7064	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD5284	Approved
0.7059	Intermediate Similarity	NPD5281	Approved
0.7048	Intermediate Similarity	NPD5173	Approved
0.7037	Intermediate Similarity	NPD4754	Approved
0.7025	Intermediate Similarity	NPD7736	Approved
0.7019	Intermediate Similarity	NPD5210	Approved
0.7019	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4629	Approved
0.7019	Intermediate Similarity	NPD5695	Phase 3
0.7009	Intermediate Similarity	NPD6319	Approved
0.6989	Remote Similarity	NPD6942	Approved
0.6989	Remote Similarity	NPD7339	Approved
0.6979	Remote Similarity	NPD4695	Discontinued
0.6957	Remote Similarity	NPD6274	Approved
0.6952	Remote Similarity	NPD7614	Phase 1
0.6947	Remote Similarity	NPD6115	Approved
0.6947	Remote Similarity	NPD6114	Approved
0.6947	Remote Similarity	NPD6697	Approved
0.6947	Remote Similarity	NPD6118	Approved
0.6937	Remote Similarity	NPD4729	Approved
0.6937	Remote Similarity	NPD4730	Approved
0.6937	Remote Similarity	NPD5128	Approved
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD5737	Approved
0.693	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.6915	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5369	Approved
0.6882	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6054	Approved
0.6864	Remote Similarity	NPD6059	Approved
0.686	Remote Similarity	NPD6616	Approved
0.6847	Remote Similarity	NPD6412	Phase 2
0.6838	Remote Similarity	NPD6335	Approved
0.6837	Remote Similarity	NPD4221	Approved
0.6837	Remote Similarity	NPD4223	Phase 3
0.6829	Remote Similarity	NPD7319	Approved
0.6814	Remote Similarity	NPD5251	Approved
0.6814	Remote Similarity	NPD5247	Approved
0.6814	Remote Similarity	NPD5248	Approved
0.6814	Remote Similarity	NPD5249	Phase 3
0.6814	Remote Similarity	NPD5250	Approved
0.6814	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6908	Approved
0.6807	Remote Similarity	NPD6909	Approved
0.6803	Remote Similarity	NPD8293	Discontinued
0.6803	Remote Similarity	NPD7078	Approved
0.68	Remote Similarity	NPD5329	Approved
0.6783	Remote Similarity	NPD8133	Approved
0.6768	Remote Similarity	NPD4788	Approved
0.6754	Remote Similarity	NPD5217	Approved
0.6754	Remote Similarity	NPD5216	Approved
0.6754	Remote Similarity	NPD5215	Approved
0.6752	Remote Similarity	NPD6009	Approved
0.6752	Remote Similarity	NPD6317	Approved
0.675	Remote Similarity	NPD6370	Approved
0.6733	Remote Similarity	NPD6098	Approved
0.6733	Remote Similarity	NPD5279	Phase 3
0.6731	Remote Similarity	NPD7637	Suspended
0.6721	Remote Similarity	NPD7507	Approved
0.67	Remote Similarity	NPD4197	Approved
0.6699	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6080	Approved
0.6699	Remote Similarity	NPD6904	Approved
0.6695	Remote Similarity	NPD6313	Approved
0.6695	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6637	Remote Similarity	NPD6686	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6636	Remote Similarity	NPD7732	Phase 3
0.6612	Remote Similarity	NPD5988	Approved
0.6609	Remote Similarity	NPD5127	Approved
0.6604	Remote Similarity	NPD6001	Approved
0.6569	Remote Similarity	NPD4519	Discontinued
0.6569	Remote Similarity	NPD4623	Approved
0.6569	Remote Similarity	NPD4688	Approved
0.6569	Remote Similarity	NPD4138	Approved
0.6569	Remote Similarity	NPD4690	Approved
0.6569	Remote Similarity	NPD5205	Approved
0.6569	Remote Similarity	NPD4693	Phase 3
0.6569	Remote Similarity	NPD4689	Approved
0.6557	Remote Similarity	NPD7604	Phase 2
0.6549	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD1698	Clinical (unspecified phase)

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