NPASS Compound

Structure

NPC474686 OpenBabel07101718192D 33 37 0 0 1 0 0 0 0 0999 V2000 2.5297 4.3816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0165 -2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0429 -2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3729 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 0.4868 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 2.5297 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2162 -1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 19 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 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 19 24 2 0 0 0 0 20 24 1 0 0 0 0 20 28 1 6 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 1 0 0 0 24 30 1 0 0 0 0 25 32 2 0 0 0 0 25 33 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 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	503.115
LogP:	5.279
LogD:	5.104
LogS:	-4.707
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.442
Synthetic Accessibility Score:	4.84
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.359
MDCK Permeability:	1.1509794603625778e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.287
Plasma Protein Binding (PPB):	90.7720718383789%
Volume Distribution (VD):	0.525
Pgp-substrate:	3.9180073738098145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.344
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.295
CYP2C9-substrate:	0.418
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.196
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	2.886
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.379
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.216
Carcinogencity:	0.031
Eye Corrosion:	0.053
Eye Irritation:	0.056
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC474686

Natural Product ID:	NPC474686
*Common Name:**	3Beta-Hydroxyrus-18,20(30)-Dien-28-Oic Acid
IUPAC Name:	(4aS,6aR,6aR,6bR,8aR,10S,12aR,14aS)-10-hydroxy-1,6a,6b,9,9,12a-hexamethyl-2-methylidene-3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a-tetradecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	DZVARQVBYAEZFI-JZQYXDLISA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h20-23,31H,1,8-17H2,2-7H3,(H,32,33)/t20-,21+,22-,23+,27+,28-,29-,30+/m1/s1
SMILES:	CC1=C2C3CCC4C5(CCC(C(C5CCC4(C3(CCC2(CCC1=C)C(=O)O)C)C)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479472
PubChem CID:	10718553
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
NPO928	Baeckea gunniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654412]

☑ 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	2
Others	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	5600.0	nM	PMID[543975]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	2500.0	nM	PMID[543975]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	82.0	%	PMID[543975]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	68.0	%	PMID[543975]

☑ 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 NPC474686 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	205
0.1-0.2	1192
0.2-0.3	4723
0.3-0.4	14250
0.4-0.5	9691
0.5-0.6	5613
0.6-0.7	4886
0.7-0.8	1642
0.8-0.85	190
0.85-0.9	158
0.9-0.95	117
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC161751
0.9762	High Similarity	NPC474972
0.9762	High Similarity	NPC95246
0.9643	High Similarity	NPC470629
0.9643	High Similarity	NPC17733
0.9643	High Similarity	NPC290690
0.9643	High Similarity	NPC473242
0.9643	High Similarity	NPC181225
0.9643	High Similarity	NPC474512
0.9535	High Similarity	NPC301244
0.9529	High Similarity	NPC470588
0.9529	High Similarity	NPC143232
0.9529	High Similarity	NPC198664
0.9529	High Similarity	NPC274330
0.9524	High Similarity	NPC130577
0.9524	High Similarity	NPC98442
0.9524	High Similarity	NPC293564
0.9524	High Similarity	NPC88716
0.9524	High Similarity	NPC142415
0.9524	High Similarity	NPC68160
0.9524	High Similarity	NPC307426
0.9524	High Similarity	NPC171203
0.9524	High Similarity	NPC102683
0.9524	High Similarity	NPC51700
0.9524	High Similarity	NPC242468
0.9524	High Similarity	NPC18064
0.9419	High Similarity	NPC470589
0.9419	High Similarity	NPC111110
0.9419	High Similarity	NPC126369
0.9412	High Similarity	NPC246708
0.9412	High Similarity	NPC40552
0.9412	High Similarity	NPC182797
0.9412	High Similarity	NPC52169
0.9405	High Similarity	NPC72638
0.9318	High Similarity	NPC80365
0.931	High Similarity	NPC187722
0.9302	High Similarity	NPC270768
0.9302	High Similarity	NPC25906
0.9302	High Similarity	NPC234346
0.9302	High Similarity	NPC121798
0.9302	High Similarity	NPC130520
0.9302	High Similarity	NPC290972
0.9302	High Similarity	NPC263393
0.9302	High Similarity	NPC61543
0.9302	High Similarity	NPC64872
0.9302	High Similarity	NPC59263
0.9302	High Similarity	NPC225585
0.9302	High Similarity	NPC293048
0.9302	High Similarity	NPC127689
0.9294	High Similarity	NPC71507
0.9205	High Similarity	NPC118519
0.9205	High Similarity	NPC202728
0.9205	High Similarity	NPC229281
0.9205	High Similarity	NPC158059
0.9195	High Similarity	NPC227467
0.9195	High Similarity	NPC86372
0.9195	High Similarity	NPC474728
0.9195	High Similarity	NPC130278
0.9195	High Similarity	NPC273621
0.9195	High Similarity	NPC477872
0.9195	High Similarity	NPC172361
0.9195	High Similarity	NPC7260
0.9195	High Similarity	NPC18872
0.9195	High Similarity	NPC210037
0.9195	High Similarity	NPC120968
0.9195	High Similarity	NPC290614
0.9195	High Similarity	NPC291028
0.9167	High Similarity	NPC171789
0.9101	High Similarity	NPC209868
0.9101	High Similarity	NPC159365
0.9101	High Similarity	NPC114159
0.9101	High Similarity	NPC191412
0.9101	High Similarity	NPC6818
0.9091	High Similarity	NPC300351
0.9091	High Similarity	NPC77099
0.9091	High Similarity	NPC155120
0.9091	High Similarity	NPC84319
0.9091	High Similarity	NPC38754
0.9091	High Similarity	NPC145067
0.9091	High Similarity	NPC324341
0.9091	High Similarity	NPC472149
0.9091	High Similarity	NPC25299
0.9091	High Similarity	NPC285184
0.9091	High Similarity	NPC4036
0.9091	High Similarity	NPC306541
0.9091	High Similarity	NPC60755
0.9091	High Similarity	NPC105189
0.9091	High Similarity	NPC233455
0.9091	High Similarity	NPC474525
0.9091	High Similarity	NPC470590
0.9091	High Similarity	NPC71074
0.9091	High Similarity	NPC158030
0.9091	High Similarity	NPC52021
0.9091	High Similarity	NPC65120
0.9091	High Similarity	NPC966
0.9091	High Similarity	NPC228784
0.9091	High Similarity	NPC282616
0.9091	High Similarity	NPC288833
0.9091	High Similarity	NPC235884
0.907	High Similarity	NPC73064
0.9059	High Similarity	NPC133954
0.9011	High Similarity	NPC21728
0.9	High Similarity	NPC473240
0.9	High Similarity	NPC96916
0.8989	High Similarity	NPC49776
0.8989	High Similarity	NPC133579
0.8989	High Similarity	NPC86368
0.8989	High Similarity	NPC298554
0.8989	High Similarity	NPC136313
0.8989	High Similarity	NPC63118
0.8989	High Similarity	NPC275809
0.8989	High Similarity	NPC307335
0.8989	High Similarity	NPC474806
0.8989	High Similarity	NPC295643
0.8989	High Similarity	NPC474436
0.8989	High Similarity	NPC272075
0.8989	High Similarity	NPC74855
0.8989	High Similarity	NPC214756
0.8977	High Similarity	NPC120840
0.8977	High Similarity	NPC113989
0.8977	High Similarity	NPC46441
0.8977	High Similarity	NPC193750
0.8977	High Similarity	NPC49320
0.8953	High Similarity	NPC74363
0.8953	High Similarity	NPC95594
0.8953	High Similarity	NPC56588
0.8953	High Similarity	NPC475862
0.8953	High Similarity	NPC235341
0.8953	High Similarity	NPC213412
0.8953	High Similarity	NPC477579
0.8941	High Similarity	NPC180834
0.8901	High Similarity	NPC207922
0.8901	High Similarity	NPC88847
0.8901	High Similarity	NPC476318
0.8901	High Similarity	NPC9487
0.8901	High Similarity	NPC157113
0.8901	High Similarity	NPC132824
0.8901	High Similarity	NPC158371
0.8901	High Similarity	NPC259733
0.8901	High Similarity	NPC327179
0.8901	High Similarity	NPC173744
0.8901	High Similarity	NPC73004
0.8901	High Similarity	NPC476327
0.8901	High Similarity	NPC116457
0.8901	High Similarity	NPC204961
0.8901	High Similarity	NPC62516
0.8889	High Similarity	NPC145667
0.8889	High Similarity	NPC299996
0.8889	High Similarity	NPC263548
0.8889	High Similarity	NPC32407
0.8889	High Similarity	NPC222047
0.8889	High Similarity	NPC20235
0.8889	High Similarity	NPC88116
0.8889	High Similarity	NPC87095
0.8889	High Similarity	NPC231063
0.8889	High Similarity	NPC282395
0.8889	High Similarity	NPC91010
0.8889	High Similarity	NPC474529
0.8876	High Similarity	NPC6255
0.8876	High Similarity	NPC475708
0.8876	High Similarity	NPC471588
0.8864	High Similarity	NPC30522
0.8864	High Similarity	NPC475049
0.8824	High Similarity	NPC70834
0.881	High Similarity	NPC473420
0.8804	High Similarity	NPC187933
0.8804	High Similarity	NPC43686
0.8804	High Similarity	NPC247139
0.8804	High Similarity	NPC189880
0.8804	High Similarity	NPC255589
0.8804	High Similarity	NPC259788
0.8804	High Similarity	NPC9613
0.8791	High Similarity	NPC32118
0.8791	High Similarity	NPC198245
0.8791	High Similarity	NPC195715
0.8791	High Similarity	NPC139570
0.8791	High Similarity	NPC148523
0.8791	High Similarity	NPC474727
0.8778	High Similarity	NPC118490
0.875	High Similarity	NPC474511
0.875	High Similarity	NPC1753
0.8736	High Similarity	NPC187545
0.8736	High Similarity	NPC329943
0.8736	High Similarity	NPC9892
0.8736	High Similarity	NPC73038
0.8736	High Similarity	NPC10005
0.8736	High Similarity	NPC325594
0.8736	High Similarity	NPC91525
0.871	High Similarity	NPC174663
0.871	High Similarity	NPC111214
0.871	High Similarity	NPC271614
0.871	High Similarity	NPC29765
0.871	High Similarity	NPC260149
0.871	High Similarity	NPC58942
0.8706	High Similarity	NPC251779
0.8706	High Similarity	NPC69101
0.8706	High Similarity	NPC310989
0.8696	High Similarity	NPC307282
0.8696	High Similarity	NPC25848
0.8696	High Similarity	NPC201657

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 NPC474686 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1532
0.2-0.3	3773
0.3-0.4	2425
0.4-0.5	771
0.5-0.6	208
0.6-0.7	220
0.7-0.8	24
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD7515	Phase 2
0.8681	High Similarity	NPD7748	Approved
0.8621	High Similarity	NPD7520	Clinical (unspecified phase)
0.8404	Intermediate Similarity	NPD7902	Approved
0.814	Intermediate Similarity	NPD7645	Phase 2
0.809	Intermediate Similarity	NPD4786	Approved
0.8085	Intermediate Similarity	NPD7900	Approved
0.8085	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD3667	Approved
0.8043	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD3618	Phase 1
0.7872	Intermediate Similarity	NPD8035	Phase 2
0.7872	Intermediate Similarity	NPD8034	Phase 2
0.7849	Intermediate Similarity	NPD5328	Approved
0.7789	Intermediate Similarity	NPD6399	Phase 3
0.7684	Intermediate Similarity	NPD6079	Approved
0.7684	Intermediate Similarity	NPD6411	Approved
0.7553	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.7474	Intermediate Similarity	NPD6101	Approved
0.7474	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4202	Approved
0.74	Intermediate Similarity	NPD7638	Approved
0.7386	Intermediate Similarity	NPD6117	Approved
0.7356	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD5279	Phase 3
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.734	Intermediate Similarity	NPD7146	Approved
0.7327	Intermediate Similarity	NPD7639	Approved
0.7327	Intermediate Similarity	NPD7640	Approved
0.7312	Intermediate Similarity	NPD3668	Phase 3
0.7308	Intermediate Similarity	NPD7128	Approved
0.7308	Intermediate Similarity	NPD5739	Approved
0.7308	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD6402	Approved
0.7303	Intermediate Similarity	NPD6116	Phase 1
0.7273	Intermediate Similarity	NPD7339	Approved
0.7273	Intermediate Similarity	NPD6942	Approved
0.7263	Intermediate Similarity	NPD3573	Approved
0.7253	Intermediate Similarity	NPD7525	Registered
0.7222	Intermediate Similarity	NPD6118	Approved
0.7222	Intermediate Similarity	NPD6115	Approved
0.7222	Intermediate Similarity	NPD6114	Approved
0.7222	Intermediate Similarity	NPD6697	Approved
0.72	Intermediate Similarity	NPD5222	Approved
0.72	Intermediate Similarity	NPD4697	Phase 3
0.72	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5221	Approved
0.7191	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6903	Approved
0.717	Intermediate Similarity	NPD7320	Approved
0.717	Intermediate Similarity	NPD6881	Approved
0.717	Intermediate Similarity	NPD6899	Approved
0.7129	Intermediate Similarity	NPD5173	Approved
0.7129	Intermediate Similarity	NPD6084	Phase 2
0.7129	Intermediate Similarity	NPD4755	Approved
0.7129	Intermediate Similarity	NPD6083	Phase 2
0.7117	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6373	Approved
0.7075	Intermediate Similarity	NPD5697	Approved
0.7075	Intermediate Similarity	NPD5701	Approved
0.7071	Intermediate Similarity	NPD5778	Approved
0.7071	Intermediate Similarity	NPD5779	Approved
0.7065	Intermediate Similarity	NPD4695	Discontinued
0.7037	Intermediate Similarity	NPD6883	Approved
0.7037	Intermediate Similarity	NPD7290	Approved
0.7037	Intermediate Similarity	NPD7102	Approved
0.703	Intermediate Similarity	NPD7614	Phase 1
0.7021	Intermediate Similarity	NPD4788	Approved
0.701	Intermediate Similarity	NPD5737	Approved
0.701	Intermediate Similarity	NPD6672	Approved
0.7009	Intermediate Similarity	NPD6011	Approved
0.699	Remote Similarity	NPD4700	Approved
0.699	Remote Similarity	NPD5286	Approved
0.699	Remote Similarity	NPD5285	Approved
0.699	Remote Similarity	NPD4696	Approved
0.6972	Remote Similarity	NPD8130	Phase 1
0.6972	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6869	Approved
0.6972	Remote Similarity	NPD6617	Approved
0.6972	Remote Similarity	NPD6649	Approved
0.6972	Remote Similarity	NPD6847	Approved
0.6972	Remote Similarity	NPD6650	Approved
0.697	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5284	Approved
0.6966	Remote Similarity	NPD6926	Approved
0.6966	Remote Similarity	NPD6924	Approved
0.6964	Remote Similarity	NPD7115	Discovery
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6939	Remote Similarity	NPD4753	Phase 2
0.6932	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5223	Approved
0.6915	Remote Similarity	NPD4223	Phase 3
0.6915	Remote Similarity	NPD4221	Approved
0.6909	Remote Similarity	NPD8297	Approved
0.6909	Remote Similarity	NPD6882	Approved
0.6897	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8328	Phase 3
0.6889	Remote Similarity	NPD8264	Approved
0.6882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5329	Approved
0.6857	Remote Similarity	NPD4633	Approved
0.6857	Remote Similarity	NPD7632	Discontinued
0.6857	Remote Similarity	NPD5226	Approved
0.6857	Remote Similarity	NPD5225	Approved
0.6857	Remote Similarity	NPD5211	Phase 2
0.6857	Remote Similarity	NPD5224	Approved
0.6848	Remote Similarity	NPD3617	Approved
0.6813	Remote Similarity	NPD6933	Approved
0.6804	Remote Similarity	NPD5280	Approved
0.6804	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4694	Approved
0.6804	Remote Similarity	NPD6098	Approved
0.6792	Remote Similarity	NPD5174	Approved
0.6792	Remote Similarity	NPD4754	Approved
0.6792	Remote Similarity	NPD5175	Approved
0.6771	Remote Similarity	NPD4197	Approved
0.6765	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5695	Phase 3
0.6742	Remote Similarity	NPD7152	Approved
0.6742	Remote Similarity	NPD7150	Approved
0.6742	Remote Similarity	NPD7151	Approved
0.6731	Remote Similarity	NPD5696	Approved
0.6731	Remote Similarity	NPD4225	Approved
0.6729	Remote Similarity	NPD5141	Approved
0.6726	Remote Similarity	NPD6868	Approved
0.6705	Remote Similarity	NPD6923	Approved
0.6705	Remote Similarity	NPD6922	Approved
0.6703	Remote Similarity	NPD3703	Phase 2
0.6702	Remote Similarity	NPD7509	Discontinued
0.6699	Remote Similarity	NPD7732	Phase 3
0.6696	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7637	Suspended
0.6634	Remote Similarity	NPD6050	Approved
0.6633	Remote Similarity	NPD4689	Approved
0.6633	Remote Similarity	NPD4138	Approved
0.6633	Remote Similarity	NPD4693	Phase 3
0.6633	Remote Similarity	NPD4688	Approved
0.6633	Remote Similarity	NPD4690	Approved
0.6633	Remote Similarity	NPD4623	Approved
0.6633	Remote Similarity	NPD5205	Approved
0.6633	Remote Similarity	NPD4519	Discontinued
0.6629	Remote Similarity	NPD7143	Approved
0.6629	Remote Similarity	NPD4245	Approved
0.6629	Remote Similarity	NPD7144	Approved
0.6629	Remote Similarity	NPD4244	Approved
0.6609	Remote Similarity	NPD6335	Approved
0.6606	Remote Similarity	NPD6412	Phase 2
0.6602	Remote Similarity	NPD5210	Approved
0.6602	Remote Similarity	NPD4629	Approved
0.66	Remote Similarity	NPD6080	Approved
0.66	Remote Similarity	NPD6673	Approved
0.66	Remote Similarity	NPD6904	Approved
0.6596	Remote Similarity	NPD6929	Approved
0.6579	Remote Similarity	NPD6274	Approved
0.6562	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD4224	Phase 2
0.6552	Remote Similarity	NPD7100	Approved
0.6549	Remote Similarity	NPD8133	Approved
0.6545	Remote Similarity	NPD4729	Approved
0.6545	Remote Similarity	NPD5168	Approved
0.6545	Remote Similarity	NPD5128	Approved
0.6545	Remote Similarity	NPD4730	Approved
0.6535	Remote Similarity	NPD5207	Approved
0.6535	Remote Similarity	NPD5692	Phase 3
0.6531	Remote Similarity	NPD1694	Approved
0.6526	Remote Similarity	NPD6931	Approved
0.6526	Remote Similarity	NPD6930	Phase 2
0.6526	Remote Similarity	NPD4748	Discontinued
0.6522	Remote Similarity	NPD8039	Approved
0.6522	Remote Similarity	NPD6009	Approved
0.6522	Remote Similarity	NPD6317	Approved
0.6517	Remote Similarity	NPD3698	Phase 2
0.6509	Remote Similarity	NPD6404	Discontinued
0.6505	Remote Similarity	NPD6001	Approved
0.65	Remote Similarity	NPD5208	Approved
0.6489	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5694	Approved
0.6466	Remote Similarity	NPD6313	Approved
0.6466	Remote Similarity	NPD6314	Approved
0.6465	Remote Similarity	NPD5690	Phase 2
0.6458	Remote Similarity	NPD4139	Approved
0.6458	Remote Similarity	NPD4692	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