NPASS Compound

Structure

NPC38754 OpenBabel07101718182D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.8425 -4.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4316 -3.7831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0186 2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0443 2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 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 -2.5315 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -3.4103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 -1.4615 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 18 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 21 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 22 1 0 0 0 0 18 28 1 0 0 0 0 19 26 1 0 0 0 0 19 27 1 1 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 26 1 0 0 0 0 21 31 2 0 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 25 1 0 0 0 0 23 32 1 6 0 0 0 24 33 2 0 0 0 0 24 34 1 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 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	5.031
LogD:	4.446
LogS:	-4.558
# Rotatable Bonds:	1
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	4.75
Fsp3:	0.867
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:	-5.406
MDCK Permeability:	1.1007856301148422e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.37
Plasma Protein Binding (PPB):	93.5886459350586%
Volume Distribution (VD):	0.644
Pgp-substrate:	4.25970983505249%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.483
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.153
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.179
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	2.645
Half-life (T1/2):	0.351

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.255
Maximum Recommended Daily Dose:	0.665
Skin Sensitization:	0.043
Carcinogencity:	0.065
Eye Corrosion:	0.089
Eye Irritation:	0.36
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC38754

Natural Product ID:	NPC38754
*Common Name:**	19-Alpha-Hydroxy-3-Oxo-Olean-12-En-28-Oic Acid
IUPAC Name:	(1S,4aR,6aR,6aS,6bR,8aR,12aR,14bS)-1-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	NFBBPROWDXTYCL-OEMDQZJXSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)14-16-30(24(33)34)17-15-28(6)18(22(30)23(25)32)8-9-20-27(5)12-11-21(31)26(3,4)19(27)10-13-29(20,28)7/h8,19-20,22-23,32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,22+,23-,27-,28+,29+,30-/m0/s1
SMILES:	OC(=O)[C@]12CC[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@]4(C)CCC(=O)C3(C)C)[C@@H]2[C@@H](C(CC1)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496075
PubChem CID:	11843702
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
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	resin	n.a.	n.a.	PMID[16724846]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12830	Styrax tonkinensis	Species	Styracaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IG50	=	41.0	uM	PMID[494297]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	<	10.0	%	PMID[494297]

☑ 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 NPC38754 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	206
0.1-0.2	1321
0.2-0.3	4913
0.3-0.4	13618
0.4-0.5	9075
0.5-0.6	5816
0.6-0.7	4989
0.7-0.8	2217
0.8-0.85	214
0.85-0.9	127
0.9-0.95	166
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC193750
0.9767	High Similarity	NPC105189
0.9767	High Similarity	NPC187722
0.9655	High Similarity	NPC229281
0.9655	High Similarity	NPC118490
0.9655	High Similarity	NPC158059
0.9655	High Similarity	NPC202728
0.9655	High Similarity	NPC118519
0.9651	High Similarity	NPC227467
0.9651	High Similarity	NPC290614
0.9651	High Similarity	NPC18872
0.9651	High Similarity	NPC7260
0.9651	High Similarity	NPC210037
0.9651	High Similarity	NPC291028
0.9651	High Similarity	NPC477872
0.9651	High Similarity	NPC120968
0.9651	High Similarity	NPC273621
0.9551	High Similarity	NPC62516
0.9551	High Similarity	NPC157113
0.9545	High Similarity	NPC148964
0.9545	High Similarity	NPC114159
0.9545	High Similarity	NPC191412
0.9545	High Similarity	NPC6818
0.9535	High Similarity	NPC274330
0.9535	High Similarity	NPC143232
0.9535	High Similarity	NPC290972
0.9535	High Similarity	NPC25906
0.9535	High Similarity	NPC198664
0.9535	High Similarity	NPC64872
0.9438	High Similarity	NPC96916
0.9425	High Similarity	NPC470589
0.9425	High Similarity	NPC111110
0.9425	High Similarity	NPC126369
0.9425	High Similarity	NPC130278
0.9419	High Similarity	NPC470629
0.9419	High Similarity	NPC290690
0.9419	High Similarity	NPC182797
0.9419	High Similarity	NPC17733
0.9419	High Similarity	NPC474512
0.9419	High Similarity	NPC181225
0.9419	High Similarity	NPC52169
0.9419	High Similarity	NPC473242
0.9333	High Similarity	NPC327179
0.9333	High Similarity	NPC73004
0.9333	High Similarity	NPC132824
0.9333	High Similarity	NPC116457
0.9333	High Similarity	NPC204961
0.9333	High Similarity	NPC158371
0.9333	High Similarity	NPC173744
0.9333	High Similarity	NPC207922
0.9333	High Similarity	NPC259733
0.9318	High Similarity	NPC65120
0.9318	High Similarity	NPC6255
0.9318	High Similarity	NPC145067
0.9318	High Similarity	NPC158030
0.9318	High Similarity	NPC233455
0.9318	High Similarity	NPC4036
0.9318	High Similarity	NPC474525
0.9318	High Similarity	NPC471588
0.931	High Similarity	NPC130520
0.931	High Similarity	NPC225585
0.931	High Similarity	NPC121798
0.931	High Similarity	NPC127689
0.931	High Similarity	NPC59263
0.931	High Similarity	NPC234346
0.931	High Similarity	NPC470588
0.931	High Similarity	NPC293048
0.931	High Similarity	NPC270768
0.931	High Similarity	NPC263393
0.931	High Similarity	NPC61543
0.9302	High Similarity	NPC242468
0.9302	High Similarity	NPC171203
0.9302	High Similarity	NPC18064
0.9302	High Similarity	NPC68160
0.9302	High Similarity	NPC73064
0.9302	High Similarity	NPC293564
0.9302	High Similarity	NPC98442
0.9302	High Similarity	NPC88716
0.9302	High Similarity	NPC142415
0.9302	High Similarity	NPC130577
0.9302	High Similarity	NPC102683
0.9302	High Similarity	NPC51700
0.9302	High Similarity	NPC307426
0.9231	High Similarity	NPC259788
0.9231	High Similarity	NPC255589
0.9231	High Similarity	NPC187933
0.9231	High Similarity	NPC247139
0.9231	High Similarity	NPC9613
0.9231	High Similarity	NPC43686
0.9222	High Similarity	NPC473240
0.9222	High Similarity	NPC139570
0.9213	High Similarity	NPC214756
0.9213	High Similarity	NPC295643
0.9213	High Similarity	NPC272075
0.9205	High Similarity	NPC46441
0.9205	High Similarity	NPC474728
0.9195	High Similarity	NPC40552
0.9195	High Similarity	NPC474511
0.9195	High Similarity	NPC246708
0.9195	High Similarity	NPC1753
0.9186	High Similarity	NPC74363
0.9186	High Similarity	NPC72638
0.9186	High Similarity	NPC475862
0.914	High Similarity	NPC118964
0.913	High Similarity	NPC174663
0.913	High Similarity	NPC111214
0.913	High Similarity	NPC271614
0.913	High Similarity	NPC29765
0.9121	High Similarity	NPC476327
0.9121	High Similarity	NPC476318
0.9111	High Similarity	NPC474529
0.9111	High Similarity	NPC32407
0.9111	High Similarity	NPC231063
0.9111	High Similarity	NPC20235
0.9111	High Similarity	NPC263548
0.9111	High Similarity	NPC299996
0.9111	High Similarity	NPC60692
0.9111	High Similarity	NPC209868
0.9111	High Similarity	NPC145667
0.9111	High Similarity	NPC282395
0.9111	High Similarity	NPC159365
0.9111	High Similarity	NPC88116
0.9101	High Similarity	NPC77099
0.9101	High Similarity	NPC235704
0.9101	High Similarity	NPC472149
0.9101	High Similarity	NPC25299
0.9101	High Similarity	NPC282616
0.9101	High Similarity	NPC155120
0.9101	High Similarity	NPC52021
0.9101	High Similarity	NPC84319
0.9101	High Similarity	NPC306541
0.9101	High Similarity	NPC285184
0.9101	High Similarity	NPC288833
0.9101	High Similarity	NPC60755
0.9101	High Similarity	NPC470590
0.9101	High Similarity	NPC235884
0.9101	High Similarity	NPC324341
0.9101	High Similarity	NPC71074
0.9101	High Similarity	NPC300351
0.9101	High Similarity	NPC228784
0.9101	High Similarity	NPC966
0.9091	High Similarity	NPC281524
0.9091	High Similarity	NPC474972
0.9091	High Similarity	NPC95246
0.9091	High Similarity	NPC474686
0.9091	High Similarity	NPC161751
0.908	High Similarity	NPC158141
0.908	High Similarity	NPC173089
0.908	High Similarity	NPC71507
0.907	High Similarity	NPC133954
0.9032	High Similarity	NPC35239
0.9022	High Similarity	NPC189880
0.9022	High Similarity	NPC106112
0.9022	High Similarity	NPC261935
0.9011	High Similarity	NPC148523
0.9011	High Similarity	NPC32118
0.9011	High Similarity	NPC83693
0.9011	High Similarity	NPC290481
0.9	High Similarity	NPC49776
0.9	High Similarity	NPC307335
0.9	High Similarity	NPC74855
0.9	High Similarity	NPC275809
0.9	High Similarity	NPC474806
0.9	High Similarity	NPC474436
0.9	High Similarity	NPC136313
0.9	High Similarity	NPC133579
0.9	High Similarity	NPC298554
0.9	High Similarity	NPC63118
0.9	High Similarity	NPC86368
0.8989	High Similarity	NPC113989
0.8989	High Similarity	NPC86372
0.8989	High Similarity	NPC172361
0.8989	High Similarity	NPC49320
0.8989	High Similarity	NPC120840
0.8977	High Similarity	NPC474474
0.8966	High Similarity	NPC56588
0.8966	High Similarity	NPC213412
0.8953	High Similarity	NPC180834
0.8941	High Similarity	NPC69101
0.8941	High Similarity	NPC310989
0.8941	High Similarity	NPC251779
0.8936	High Similarity	NPC233012
0.8936	High Similarity	NPC256247
0.8936	High Similarity	NPC54909
0.8925	High Similarity	NPC58942
0.8925	High Similarity	NPC260149
0.8925	High Similarity	NPC164349
0.8925	High Similarity	NPC471966
0.8913	High Similarity	NPC98874
0.8913	High Similarity	NPC19376
0.8913	High Similarity	NPC305464
0.8913	High Similarity	NPC25848
0.8913	High Similarity	NPC307282
0.8913	High Similarity	NPC201657
0.8901	High Similarity	NPC91010
0.8901	High Similarity	NPC80365
0.8901	High Similarity	NPC222047
0.8901	High Similarity	NPC74751
0.8901	High Similarity	NPC87095
0.8889	High Similarity	NPC301244

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 NPC38754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1666
0.2-0.3	3812
0.3-0.4	2297
0.4-0.5	715
0.5-0.6	208
0.6-0.7	199
0.7-0.8	58
0.8-0.85	3
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9318	High Similarity	NPD7515	Phase 2
0.9022	High Similarity	NPD7902	Approved
0.8901	High Similarity	NPD7748	Approved
0.8696	High Similarity	NPD7900	Approved
0.8696	High Similarity	NPD7901	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6399	Phase 3
0.8222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD3618	Phase 1
0.8111	Intermediate Similarity	NPD4786	Approved
0.809	Intermediate Similarity	NPD3667	Approved
0.8085	Intermediate Similarity	NPD8035	Phase 2
0.8085	Intermediate Similarity	NPD8034	Phase 2
0.8065	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7645	Phase 2
0.7872	Intermediate Similarity	NPD5328	Approved
0.7766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD3666	Approved
0.7717	Intermediate Similarity	NPD3133	Approved
0.7717	Intermediate Similarity	NPD3665	Phase 1
0.7708	Intermediate Similarity	NPD6079	Approved
0.767	Intermediate Similarity	NPD7128	Approved
0.767	Intermediate Similarity	NPD5739	Approved
0.767	Intermediate Similarity	NPD6675	Approved
0.767	Intermediate Similarity	NPD6402	Approved
0.7629	Intermediate Similarity	NPD4202	Approved
0.7619	Intermediate Similarity	NPD6372	Approved
0.7619	Intermediate Similarity	NPD6373	Approved
0.7576	Intermediate Similarity	NPD4697	Phase 3
0.7553	Intermediate Similarity	NPD6409	Approved
0.7553	Intermediate Similarity	NPD7146	Approved
0.7553	Intermediate Similarity	NPD6684	Approved
0.7553	Intermediate Similarity	NPD7521	Approved
0.7553	Intermediate Similarity	NPD7334	Approved
0.7553	Intermediate Similarity	NPD5330	Approved
0.7527	Intermediate Similarity	NPD3668	Phase 3
0.7526	Intermediate Similarity	NPD6411	Approved
0.7524	Intermediate Similarity	NPD6899	Approved
0.7524	Intermediate Similarity	NPD6881	Approved
0.7524	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7473	Intermediate Similarity	NPD4695	Discontinued
0.7473	Intermediate Similarity	NPD7525	Registered
0.7453	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5697	Approved
0.7429	Intermediate Similarity	NPD5701	Approved
0.7426	Intermediate Similarity	NPD7638	Approved
0.74	Intermediate Similarity	NPD7614	Phase 1
0.74	Intermediate Similarity	NPD5222	Approved
0.74	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5221	Approved
0.7396	Intermediate Similarity	NPD5737	Approved
0.7396	Intermediate Similarity	NPD6903	Approved
0.7396	Intermediate Similarity	NPD6672	Approved
0.7383	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD6883	Approved
0.7383	Intermediate Similarity	NPD7102	Approved
0.7368	Intermediate Similarity	NPD8328	Phase 3
0.7368	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6011	Approved
0.7353	Intermediate Similarity	NPD5286	Approved
0.7353	Intermediate Similarity	NPD5285	Approved
0.7353	Intermediate Similarity	NPD4700	Approved
0.7353	Intermediate Similarity	NPD4696	Approved
0.7353	Intermediate Similarity	NPD7639	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD5284	Approved
0.7347	Intermediate Similarity	NPD5281	Approved
0.7333	Intermediate Similarity	NPD6116	Phase 1
0.7327	Intermediate Similarity	NPD5173	Approved
0.732	Intermediate Similarity	NPD6101	Approved
0.732	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4753	Phase 2
0.7315	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6869	Approved
0.7315	Intermediate Similarity	NPD8130	Phase 1
0.7315	Intermediate Similarity	NPD6847	Approved
0.7315	Intermediate Similarity	NPD6617	Approved
0.73	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7297	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3573	Approved
0.729	Intermediate Similarity	NPD6014	Approved
0.729	Intermediate Similarity	NPD6012	Approved
0.729	Intermediate Similarity	NPD6013	Approved
0.7282	Intermediate Similarity	NPD5223	Approved
0.7255	Intermediate Similarity	NPD5696	Approved
0.7248	Intermediate Similarity	NPD8297	Approved
0.7248	Intermediate Similarity	NPD6882	Approved
0.7222	Intermediate Similarity	NPD6117	Approved
0.7212	Intermediate Similarity	NPD5224	Approved
0.7212	Intermediate Similarity	NPD5225	Approved
0.7212	Intermediate Similarity	NPD4633	Approved
0.7212	Intermediate Similarity	NPD5226	Approved
0.7212	Intermediate Similarity	NPD5211	Phase 2
0.7188	Intermediate Similarity	NPD5279	Phase 3
0.717	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD5174	Approved
0.7129	Intermediate Similarity	NPD5210	Approved
0.7129	Intermediate Similarity	NPD4629	Approved
0.7129	Intermediate Similarity	NPD5695	Phase 3
0.7128	Intermediate Similarity	NPD4221	Approved
0.7128	Intermediate Similarity	NPD4223	Phase 3
0.7111	Intermediate Similarity	NPD7339	Approved
0.7111	Intermediate Similarity	NPD6942	Approved
0.7103	Intermediate Similarity	NPD6412	Phase 2
0.7083	Intermediate Similarity	NPD5329	Approved
0.7075	Intermediate Similarity	NPD5141	Approved
0.7065	Intermediate Similarity	NPD6115	Approved
0.7065	Intermediate Similarity	NPD6697	Approved
0.7065	Intermediate Similarity	NPD6118	Approved
0.7065	Intermediate Similarity	NPD6114	Approved
0.7059	Intermediate Similarity	NPD7732	Phase 3
0.7053	Intermediate Similarity	NPD4788	Approved
0.7033	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4632	Approved
0.701	Intermediate Similarity	NPD6098	Approved
0.7009	Intermediate Similarity	NPD4768	Approved
0.7009	Intermediate Similarity	NPD4767	Approved
0.7	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4197	Approved
0.697	Remote Similarity	NPD6673	Approved
0.697	Remote Similarity	NPD6080	Approved
0.697	Remote Similarity	NPD6904	Approved
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.693	Remote Similarity	NPD6335	Approved
0.6923	Remote Similarity	NPD4225	Approved
0.6907	Remote Similarity	NPD1694	Approved
0.6903	Remote Similarity	NPD6274	Approved
0.6903	Remote Similarity	NPD6868	Approved
0.6882	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3617	Approved
0.6881	Remote Similarity	NPD4729	Approved
0.6881	Remote Similarity	NPD5128	Approved
0.6881	Remote Similarity	NPD4730	Approved
0.687	Remote Similarity	NPD7101	Approved
0.687	Remote Similarity	NPD7100	Approved
0.6863	Remote Similarity	NPD6001	Approved
0.6842	Remote Similarity	NPD6317	Approved
0.6842	Remote Similarity	NPD5369	Approved
0.6842	Remote Similarity	NPD6009	Approved
0.6837	Remote Similarity	NPD4693	Phase 3
0.6837	Remote Similarity	NPD4689	Approved
0.6837	Remote Similarity	NPD4623	Approved
0.6837	Remote Similarity	NPD4519	Discontinued
0.6837	Remote Similarity	NPD4688	Approved
0.6837	Remote Similarity	NPD5205	Approved
0.6837	Remote Similarity	NPD4690	Approved
0.6837	Remote Similarity	NPD4138	Approved
0.6783	Remote Similarity	NPD6314	Approved
0.6783	Remote Similarity	NPD6313	Approved
0.6778	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4269	Approved
0.6771	Remote Similarity	NPD4270	Approved
0.6771	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4634	Approved
0.6757	Remote Similarity	NPD5169	Approved
0.6757	Remote Similarity	NPD5249	Phase 3
0.6757	Remote Similarity	NPD5135	Approved
0.6757	Remote Similarity	NPD5247	Approved
0.6757	Remote Similarity	NPD5250	Approved
0.6757	Remote Similarity	NPD5251	Approved
0.6757	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5248	Approved
0.6752	Remote Similarity	NPD6909	Approved
0.6752	Remote Similarity	NPD6908	Approved
0.6752	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5368	Approved
0.6737	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7632	Discontinued
0.6727	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5168	Approved
0.6727	Remote Similarity	NPD6686	Approved
0.67	Remote Similarity	NPD5208	Approved
0.6696	Remote Similarity	NPD5217	Approved
0.6696	Remote Similarity	NPD5216	Approved
0.6696	Remote Similarity	NPD5215	Approved
0.6696	Remote Similarity	NPD5127	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7604	Phase 2
0.663	Remote Similarity	NPD6926	Approved
0.663	Remote Similarity	NPD6924	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