NPASS Compound

Structure

NPC474972 OpenBabel07101719252D 33 37 0 0 1 0 0 0 0 0999 V2000 -4.4682 -0.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9887 1.0796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5034 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 -0.6173 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 -0.0000 0.9737 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 1.6865 0.0000 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 -2.4342 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 -4.2162 1.4605 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 1.9474 0.0000 C 0 0 0 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 -0.0000 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 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 0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -2.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 0.4868 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 0.8432 -1.4605 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 3.3729 -2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 2.9211 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 19 2 0 0 0 0 9 22 2 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 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 20 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 30 1 1 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 0 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 32 2 0 0 0 0 24 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 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	503.115
LogP:	6.228
LogD:	4.509
LogS:	-4.579
# 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:	4.784
Fsp3:	0.833
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:	-5.429
MDCK Permeability:	1.757618156261742e-05
Pgp-inhibitor:	0.325
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.279
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.28
Plasma Protein Binding (PPB):	94.91284942626953%
Volume Distribution (VD):	0.69
Pgp-substrate:	5.387095928192139%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.565
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.252
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.237
CYP3A4-substrate:	0.801

ADMET: Excretion

Clearance (CL):	2.343
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.628
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.804
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.083
Carcinogencity:	0.493
Eye Corrosion:	0.03
Eye Irritation:	0.048
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC474972

Natural Product ID:	NPC474972
*Common Name:**	Eucalyptanoic Acid
IUPAC Name:	(4aS,6aR,6bS,8aR,10S,12aS,14bR)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,14b-dodecahydropicene-4a-carboxylic acid
Synonyms:	eucalyptanoic acid
Standard InCHIKey:	KICUTMUDQMLBSF-CYDBUDFLSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8-9,20-21,23,31H,10-18H2,1-7H3,(H,32,33)/t20-,21+,23+,27+,28-,29-,30+/m1/s1
SMILES:	CC1(CCC2(CCC3(C(=CC=C4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490537
PubChem CID:	637092
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
NPO10849.2	Eucalyptus camaldulensis	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12502346]

☑ 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
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1268	Tissue	Jejunum	Oryctolagus cuniculus	Inhibition	=	58.2	%	PMID[495427]
NPT1268	Tissue	Jejunum	Oryctolagus cuniculus	Inhibition	=	31.1	%	PMID[495427]

☑ 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 NPC474972 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	202
0.1-0.2	1149
0.2-0.3	4656
0.3-0.4	14249
0.4-0.5	9658
0.5-0.6	5653
0.6-0.7	4809
0.7-0.8	1800
0.8-0.85	176
0.85-0.9	157
0.9-0.95	135
0.95-1	53

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC95246
1.0	High Similarity	NPC161751
0.9762	High Similarity	NPC474686
0.9759	High Similarity	NPC98442
0.9759	High Similarity	NPC307426
0.9759	High Similarity	NPC293564
0.9759	High Similarity	NPC130577
0.9759	High Similarity	NPC88716
0.9759	High Similarity	NPC68160
0.9759	High Similarity	NPC242468
0.9759	High Similarity	NPC51700
0.9759	High Similarity	NPC171203
0.9759	High Similarity	NPC142415
0.9759	High Similarity	NPC18064
0.9759	High Similarity	NPC102683
0.9643	High Similarity	NPC290690
0.9643	High Similarity	NPC17733
0.9643	High Similarity	NPC470629
0.9643	High Similarity	NPC246708
0.9643	High Similarity	NPC473242
0.9643	High Similarity	NPC182797
0.9643	High Similarity	NPC52169
0.9643	High Similarity	NPC40552
0.9643	High Similarity	NPC181225
0.9643	High Similarity	NPC474512
0.9639	High Similarity	NPC72638
0.9535	High Similarity	NPC301244
0.9529	High Similarity	NPC59263
0.9529	High Similarity	NPC470588
0.9529	High Similarity	NPC270768
0.9529	High Similarity	NPC143232
0.9529	High Similarity	NPC293048
0.9529	High Similarity	NPC290972
0.9529	High Similarity	NPC61543
0.9529	High Similarity	NPC25906
0.9529	High Similarity	NPC198664
0.9529	High Similarity	NPC64872
0.9529	High Similarity	NPC127689
0.9529	High Similarity	NPC130520
0.9529	High Similarity	NPC225585
0.9529	High Similarity	NPC234346
0.9529	High Similarity	NPC121798
0.9529	High Similarity	NPC263393
0.9529	High Similarity	NPC274330
0.9419	High Similarity	NPC7260
0.9419	High Similarity	NPC126369
0.9419	High Similarity	NPC290614
0.9419	High Similarity	NPC130278
0.9419	High Similarity	NPC86372
0.9419	High Similarity	NPC470589
0.9419	High Similarity	NPC172361
0.9419	High Similarity	NPC210037
0.9419	High Similarity	NPC111110
0.9419	High Similarity	NPC477872
0.9419	High Similarity	NPC18872
0.9419	High Similarity	NPC227467
0.9419	High Similarity	NPC120968
0.9419	High Similarity	NPC291028
0.9419	High Similarity	NPC273621
0.9318	High Similarity	NPC80365
0.931	High Similarity	NPC306541
0.931	High Similarity	NPC300351
0.931	High Similarity	NPC474525
0.931	High Similarity	NPC233455
0.931	High Similarity	NPC472149
0.931	High Similarity	NPC4036
0.931	High Similarity	NPC324341
0.931	High Similarity	NPC71074
0.931	High Similarity	NPC235884
0.931	High Similarity	NPC282616
0.931	High Similarity	NPC65120
0.931	High Similarity	NPC966
0.931	High Similarity	NPC288833
0.931	High Similarity	NPC84319
0.931	High Similarity	NPC228784
0.931	High Similarity	NPC187722
0.931	High Similarity	NPC105189
0.931	High Similarity	NPC25299
0.931	High Similarity	NPC158030
0.931	High Similarity	NPC52021
0.931	High Similarity	NPC145067
0.931	High Similarity	NPC155120
0.9294	High Similarity	NPC71507
0.9286	High Similarity	NPC133954
0.9205	High Similarity	NPC136313
0.9205	High Similarity	NPC474436
0.9205	High Similarity	NPC63118
0.9205	High Similarity	NPC118519
0.9205	High Similarity	NPC202728
0.9205	High Similarity	NPC295643
0.9205	High Similarity	NPC272075
0.9205	High Similarity	NPC49776
0.9205	High Similarity	NPC214756
0.9205	High Similarity	NPC86368
0.9205	High Similarity	NPC158059
0.9205	High Similarity	NPC229281
0.9205	High Similarity	NPC275809
0.9205	High Similarity	NPC74855
0.9205	High Similarity	NPC307335
0.9205	High Similarity	NPC298554
0.9195	High Similarity	NPC474728
0.9195	High Similarity	NPC46441
0.9195	High Similarity	NPC193750
0.9195	High Similarity	NPC120840
0.9195	High Similarity	NPC49320
0.9195	High Similarity	NPC113989
0.9176	High Similarity	NPC95594
0.9176	High Similarity	NPC213412
0.9176	High Similarity	NPC74363
0.9176	High Similarity	NPC477579
0.9176	High Similarity	NPC235341
0.9176	High Similarity	NPC475862
0.9167	High Similarity	NPC171789
0.9101	High Similarity	NPC209868
0.9101	High Similarity	NPC299996
0.9101	High Similarity	NPC145667
0.9101	High Similarity	NPC282395
0.9101	High Similarity	NPC159365
0.9101	High Similarity	NPC114159
0.9101	High Similarity	NPC88116
0.9101	High Similarity	NPC191412
0.9101	High Similarity	NPC6818
0.9101	High Similarity	NPC222047
0.9101	High Similarity	NPC91010
0.9101	High Similarity	NPC32407
0.9101	High Similarity	NPC231063
0.9101	High Similarity	NPC20235
0.9101	High Similarity	NPC474529
0.9101	High Similarity	NPC263548
0.9091	High Similarity	NPC77099
0.9091	High Similarity	NPC38754
0.9091	High Similarity	NPC285184
0.9091	High Similarity	NPC6255
0.9091	High Similarity	NPC60755
0.9091	High Similarity	NPC475708
0.9091	High Similarity	NPC471588
0.9091	High Similarity	NPC470590
0.908	High Similarity	NPC30522
0.908	High Similarity	NPC475049
0.907	High Similarity	NPC73064
0.9048	High Similarity	NPC70834
0.9011	High Similarity	NPC21728
0.9	High Similarity	NPC148523
0.9	High Similarity	NPC473240
0.9	High Similarity	NPC139570
0.9	High Similarity	NPC96916
0.9	High Similarity	NPC198245
0.9	High Similarity	NPC474727
0.8989	High Similarity	NPC133579
0.8989	High Similarity	NPC118490
0.8989	High Similarity	NPC474806
0.8953	High Similarity	NPC325594
0.8953	High Similarity	NPC73038
0.8953	High Similarity	NPC10005
0.8953	High Similarity	NPC91525
0.8953	High Similarity	NPC9892
0.8953	High Similarity	NPC329943
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	NPC98874
0.8901	High Similarity	NPC201657
0.8901	High Similarity	NPC158371
0.8901	High Similarity	NPC259733
0.8901	High Similarity	NPC327179
0.8901	High Similarity	NPC173744
0.8901	High Similarity	NPC62516
0.8901	High Similarity	NPC19376
0.8901	High Similarity	NPC230151
0.8901	High Similarity	NPC305464
0.8901	High Similarity	NPC73004
0.8901	High Similarity	NPC25848
0.8901	High Similarity	NPC476327
0.8901	High Similarity	NPC116457
0.8901	High Similarity	NPC204961
0.8901	High Similarity	NPC307282
0.8889	High Similarity	NPC87095
0.8889	High Similarity	NPC296164
0.8889	High Similarity	NPC60692
0.8889	High Similarity	NPC74751
0.8889	High Similarity	NPC184006
0.8889	High Similarity	NPC78580
0.8889	High Similarity	NPC188102
0.8889	High Similarity	NPC23621
0.8864	High Similarity	NPC77168
0.8864	High Similarity	NPC84271
0.8864	High Similarity	NPC102414
0.8864	High Similarity	NPC69627
0.8864	High Similarity	NPC281524
0.8851	High Similarity	NPC46912
0.8851	High Similarity	NPC158141
0.8851	High Similarity	NPC142361
0.8851	High Similarity	NPC474684
0.8851	High Similarity	NPC173089
0.8851	High Similarity	NPC162107
0.8837	High Similarity	NPC191965

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 NPC474972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1452
0.2-0.3	3791
0.3-0.4	2465
0.4-0.5	784
0.5-0.6	208
0.6-0.7	219
0.7-0.8	41
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.931	High Similarity	NPD7515	Phase 2
0.8889	High Similarity	NPD7748	Approved
0.8621	High Similarity	NPD7520	Clinical (unspecified phase)
0.8602	High Similarity	NPD7902	Approved
0.8353	Intermediate Similarity	NPD7645	Phase 2
0.828	Intermediate Similarity	NPD7900	Approved
0.828	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD3618	Phase 1
0.809	Intermediate Similarity	NPD4786	Approved
0.8068	Intermediate Similarity	NPD3667	Approved
0.8043	Intermediate Similarity	NPD5328	Approved
0.8043	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6079	Approved
0.7872	Intermediate Similarity	NPD8035	Phase 2
0.7872	Intermediate Similarity	NPD8034	Phase 2
0.7789	Intermediate Similarity	NPD6399	Phase 3
0.7742	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3666	Approved
0.7692	Intermediate Similarity	NPD3665	Phase 1
0.7692	Intermediate Similarity	NPD3133	Approved
0.7684	Intermediate Similarity	NPD6411	Approved
0.7604	Intermediate Similarity	NPD4202	Approved
0.7576	Intermediate Similarity	NPD7638	Approved
0.7527	Intermediate Similarity	NPD6684	Approved
0.7527	Intermediate Similarity	NPD7334	Approved
0.7527	Intermediate Similarity	NPD5330	Approved
0.7527	Intermediate Similarity	NPD6409	Approved
0.7527	Intermediate Similarity	NPD7146	Approved
0.7527	Intermediate Similarity	NPD7521	Approved
0.7527	Intermediate Similarity	NPD5279	Phase 3
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7476	Intermediate Similarity	NPD5739	Approved
0.7476	Intermediate Similarity	NPD6675	Approved
0.7476	Intermediate Similarity	NPD7128	Approved
0.7476	Intermediate Similarity	NPD6402	Approved
0.7474	Intermediate Similarity	NPD6101	Approved
0.7474	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3573	Approved
0.7444	Intermediate Similarity	NPD7525	Registered
0.7386	Intermediate Similarity	NPD6117	Approved
0.7374	Intermediate Similarity	NPD5221	Approved
0.7374	Intermediate Similarity	NPD5222	Approved
0.7374	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4697	Phase 3
0.7368	Intermediate Similarity	NPD6903	Approved
0.7356	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6899	Approved
0.7333	Intermediate Similarity	NPD7320	Approved
0.7312	Intermediate Similarity	NPD3668	Phase 3
0.7303	Intermediate Similarity	NPD6116	Phase 1
0.73	Intermediate Similarity	NPD6083	Phase 2
0.73	Intermediate Similarity	NPD5173	Approved
0.73	Intermediate Similarity	NPD6084	Phase 2
0.73	Intermediate Similarity	NPD4755	Approved
0.7273	Intermediate Similarity	NPD6942	Approved
0.7273	Intermediate Similarity	NPD7339	Approved
0.7264	Intermediate Similarity	NPD6372	Approved
0.7264	Intermediate Similarity	NPD6373	Approved
0.7238	Intermediate Similarity	NPD5701	Approved
0.7238	Intermediate Similarity	NPD5697	Approved
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	NPD7614	Phase 1
0.7196	Intermediate Similarity	NPD7290	Approved
0.7196	Intermediate Similarity	NPD7102	Approved
0.7196	Intermediate Similarity	NPD6883	Approved
0.7191	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5737	Approved
0.7188	Intermediate Similarity	NPD6672	Approved
0.717	Intermediate Similarity	NPD6011	Approved
0.7157	Intermediate Similarity	NPD5285	Approved
0.7157	Intermediate Similarity	NPD5286	Approved
0.7157	Intermediate Similarity	NPD4700	Approved
0.7157	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.713	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6869	Approved
0.713	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD8130	Phase 1
0.713	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD6847	Approved
0.7113	Intermediate Similarity	NPD4753	Phase 2
0.7103	Intermediate Similarity	NPD6013	Approved
0.7103	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6014	Approved
0.7103	Intermediate Similarity	NPD6012	Approved
0.7097	Intermediate Similarity	NPD4221	Approved
0.7097	Intermediate Similarity	NPD4223	Phase 3
0.7087	Intermediate Similarity	NPD5223	Approved
0.7071	Intermediate Similarity	NPD5779	Approved
0.7071	Intermediate Similarity	NPD5778	Approved
0.7065	Intermediate Similarity	NPD4695	Discontinued
0.7064	Intermediate Similarity	NPD6882	Approved
0.7064	Intermediate Similarity	NPD8297	Approved
0.7053	Intermediate Similarity	NPD5329	Approved
0.7043	Intermediate Similarity	NPD8328	Phase 3
0.7021	Intermediate Similarity	NPD4788	Approved
0.7019	Intermediate Similarity	NPD5225	Approved
0.7019	Intermediate Similarity	NPD5226	Approved
0.7019	Intermediate Similarity	NPD4633	Approved
0.7019	Intermediate Similarity	NPD5224	Approved
0.7019	Intermediate Similarity	NPD5211	Phase 2
0.6979	Remote Similarity	NPD6098	Approved
0.6979	Remote Similarity	NPD5280	Approved
0.6979	Remote Similarity	NPD4694	Approved
0.6979	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6926	Approved
0.6966	Remote Similarity	NPD6924	Approved
0.6964	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7115	Discovery
0.6952	Remote Similarity	NPD5174	Approved
0.6952	Remote Similarity	NPD5175	Approved
0.6952	Remote Similarity	NPD4754	Approved
0.6947	Remote Similarity	NPD4197	Approved
0.6932	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5695	Phase 3
0.6931	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5696	Approved
0.6889	Remote Similarity	NPD8264	Approved
0.6887	Remote Similarity	NPD5141	Approved
0.6882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6868	Approved
0.6863	Remote Similarity	NPD7732	Phase 3
0.6857	Remote Similarity	NPD7632	Discontinued
0.6848	Remote Similarity	NPD3617	Approved
0.6847	Remote Similarity	NPD4632	Approved
0.6822	Remote Similarity	NPD4767	Approved
0.6822	Remote Similarity	NPD4768	Approved
0.6813	Remote Similarity	NPD6933	Approved
0.6804	Remote Similarity	NPD4138	Approved
0.6804	Remote Similarity	NPD5205	Approved
0.6804	Remote Similarity	NPD4688	Approved
0.6804	Remote Similarity	NPD4689	Approved
0.6804	Remote Similarity	NPD4623	Approved
0.6804	Remote Similarity	NPD4519	Discontinued
0.6804	Remote Similarity	NPD4690	Approved
0.6804	Remote Similarity	NPD4693	Phase 3
0.68	Remote Similarity	NPD6050	Approved
0.6768	Remote Similarity	NPD6673	Approved
0.6768	Remote Similarity	NPD6080	Approved
0.6768	Remote Similarity	NPD6904	Approved
0.6765	Remote Similarity	NPD5210	Approved
0.6765	Remote Similarity	NPD4629	Approved
0.6759	Remote Similarity	NPD6412	Phase 2
0.6754	Remote Similarity	NPD6335	Approved
0.6742	Remote Similarity	NPD7152	Approved
0.6742	Remote Similarity	NPD7151	Approved
0.6742	Remote Similarity	NPD7150	Approved
0.6737	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4225	Approved
0.6726	Remote Similarity	NPD6274	Approved
0.6705	Remote Similarity	NPD6923	Approved
0.6705	Remote Similarity	NPD6922	Approved
0.6703	Remote Similarity	NPD8039	Approved
0.6703	Remote Similarity	NPD3703	Phase 2
0.6702	Remote Similarity	NPD7509	Discontinued
0.6701	Remote Similarity	NPD1694	Approved
0.67	Remote Similarity	NPD5692	Phase 3
0.67	Remote Similarity	NPD5207	Approved
0.6697	Remote Similarity	NPD5168	Approved
0.6697	Remote Similarity	NPD4730	Approved
0.6697	Remote Similarity	NPD4729	Approved
0.6697	Remote Similarity	NPD5128	Approved
0.6696	Remote Similarity	NPD7100	Approved
0.6696	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7637	Suspended
0.6634	Remote Similarity	NPD5694	Approved
0.6633	Remote Similarity	NPD5690	Phase 2
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	NPD6313	Approved
0.6609	Remote Similarity	NPD6314	Approved
0.6596	Remote Similarity	NPD6929	Approved
0.6593	Remote Similarity	NPD4058	Approved
0.6593	Remote Similarity	NPD5733	Approved
0.6581	Remote Similarity	NPD6909	Approved
0.6581	Remote Similarity	NPD6908	Approved
0.6577	Remote Similarity	NPD4634	Approved
0.6577	Remote Similarity	NPD5250	Approved
0.6577	Remote Similarity	NPD5248	Approved
0.6577	Remote Similarity	NPD5169	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