NPASS Compound

Structure

NPC472746 OpenBabel07101718302D 22 24 0 0 1 0 0 0 0 0999 V2000 3.8228 2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3914 0.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8569 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 7 1 6 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 18 1 0 0 0 0 15 20 1 1 0 0 0 16 18 1 0 0 0 0 16 22 1 1 0 0 0 17 20 1 1 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	4.029
LogD:	4.018
LogS:	-3.851
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	4.533
Fsp3:	0.85
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:	-4.778
MDCK Permeability:	1.7114853108068928e-05
Pgp-inhibitor:	0.878
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	66.5938491821289%
Volume Distribution (VD):	0.914
Pgp-substrate:	26.10889434814453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.356
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.341
CYP2C9-substrate:	0.322
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.664
CYP3A4-inhibitor:	0.873
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	12.652
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.349
Maximum Recommended Daily Dose:	0.817
Skin Sensitization:	0.059
Carcinogencity:	0.018
Eye Corrosion:	0.013
Eye Irritation:	0.051
Respiratory Toxicity:	0.797

Download Data

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

Natural Product: NPC472746

Natural Product ID:	NPC472746
*Common Name:**	CBERMJGZJKAJQG-QKAWHGFOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CBERMJGZJKAJQG-QKAWHGFOSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-6-19(4)11-13-7-8-15-18(2,3)16(22)9-10-20(15,5)17(13)14(21)12-19/h6,13,15-17,22H,1,7-12H2,2-5H3/t13-,15-,16-,17+,19+,20-/m0/s1
SMILES:	CC1(C2CCC3CC(CC(=O)C3C2(CCC1O)C)(C)C=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581992
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32573	dysoxylum gotadhora	Species	Meliaceae	Eukaryota	Leaves and Twigs	n.a.	n.a.	PMID[25945867]

☑ 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
Others	5

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	41.5	%	PMID[566122]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	63.8	%	PMID[566122]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	92.4	%	PMID[566122]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14500.0	nM	PMID[566122]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	25.6	%	PMID[566122]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	19.8	%	PMID[566122]

☑ 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 NPC472746 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	179
0.1-0.2	1606
0.2-0.3	6485
0.3-0.4	16384
0.4-0.5	7303
0.5-0.6	5236
0.6-0.7	3815
0.7-0.8	1523
0.8-0.85	152
0.85-0.9	10
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9306	High Similarity	NPC162164
0.9041	High Similarity	NPC38426
0.88	High Similarity	NPC104806
0.875	High Similarity	NPC133954
0.875	High Similarity	NPC210323
0.8734	High Similarity	NPC475726
0.8734	High Similarity	NPC472743
0.8718	High Similarity	NPC328264
0.8684	High Similarity	NPC149249
0.8642	High Similarity	NPC475862
0.8642	High Similarity	NPC74363
0.8642	High Similarity	NPC213412
0.8625	High Similarity	NPC474482
0.8625	High Similarity	NPC475745
0.8611	High Similarity	NPC2648
0.8608	High Similarity	NPC48362
0.8537	High Similarity	NPC73064
0.8519	High Similarity	NPC76518
0.8519	High Similarity	NPC292553
0.85	High Similarity	NPC291320
0.85	High Similarity	NPC471036
0.8462	Intermediate Similarity	NPC476812
0.8434	Intermediate Similarity	NPC193360
0.8434	Intermediate Similarity	NPC472802
0.8415	Intermediate Similarity	NPC95594
0.8415	Intermediate Similarity	NPC472738
0.8415	Intermediate Similarity	NPC72638
0.8415	Intermediate Similarity	NPC158393
0.8415	Intermediate Similarity	NPC235341
0.8415	Intermediate Similarity	NPC477579
0.84	Intermediate Similarity	NPC282905
0.84	Intermediate Similarity	NPC68426
0.84	Intermediate Similarity	NPC477229
0.84	Intermediate Similarity	NPC232112
0.8395	Intermediate Similarity	NPC74595
0.8395	Intermediate Similarity	NPC180834
0.8395	Intermediate Similarity	NPC474233
0.8395	Intermediate Similarity	NPC146683
0.8395	Intermediate Similarity	NPC264665
0.8375	Intermediate Similarity	NPC110780
0.8354	Intermediate Similarity	NPC164999
0.8353	Intermediate Similarity	NPC272746
0.8353	Intermediate Similarity	NPC473167
0.8333	Intermediate Similarity	NPC69627
0.8313	Intermediate Similarity	NPC68160
0.8313	Intermediate Similarity	NPC102683
0.8313	Intermediate Similarity	NPC142415
0.8313	Intermediate Similarity	NPC51700
0.8313	Intermediate Similarity	NPC242468
0.8313	Intermediate Similarity	NPC4643
0.8313	Intermediate Similarity	NPC171203
0.8313	Intermediate Similarity	NPC18064
0.8313	Intermediate Similarity	NPC141292
0.8313	Intermediate Similarity	NPC307426
0.8313	Intermediate Similarity	NPC98442
0.8313	Intermediate Similarity	NPC293564
0.8313	Intermediate Similarity	NPC130577
0.8313	Intermediate Similarity	NPC57469
0.8313	Intermediate Similarity	NPC88716
0.8293	Intermediate Similarity	NPC294438
0.8293	Intermediate Similarity	NPC471034
0.8293	Intermediate Similarity	NPC470574
0.8293	Intermediate Similarity	NPC190704
0.8293	Intermediate Similarity	NPC264317
0.8289	Intermediate Similarity	NPC159325
0.8289	Intermediate Similarity	NPC168511
0.8272	Intermediate Similarity	NPC118800
0.8267	Intermediate Similarity	NPC156277
0.8267	Intermediate Similarity	NPC58057
0.8267	Intermediate Similarity	NPC89310
0.8267	Intermediate Similarity	NPC320549
0.8267	Intermediate Similarity	NPC151018
0.825	Intermediate Similarity	NPC3915
0.825	Intermediate Similarity	NPC473217
0.825	Intermediate Similarity	NPC14151
0.8243	Intermediate Similarity	NPC213178
0.8243	Intermediate Similarity	NPC131892
0.8243	Intermediate Similarity	NPC6120
0.8243	Intermediate Similarity	NPC327728
0.8235	Intermediate Similarity	NPC291028
0.8235	Intermediate Similarity	NPC85173
0.8235	Intermediate Similarity	NPC126993
0.8228	Intermediate Similarity	NPC201459
0.8228	Intermediate Similarity	NPC474113
0.8219	Intermediate Similarity	NPC472984
0.8214	Intermediate Similarity	NPC182797
0.8214	Intermediate Similarity	NPC474719
0.8214	Intermediate Similarity	NPC40552
0.8214	Intermediate Similarity	NPC310752
0.8214	Intermediate Similarity	NPC181225
0.8214	Intermediate Similarity	NPC52169
0.8214	Intermediate Similarity	NPC246708
0.8214	Intermediate Similarity	NPC474677
0.8214	Intermediate Similarity	NPC474512
0.8214	Intermediate Similarity	NPC206060
0.8214	Intermediate Similarity	NPC473242
0.8214	Intermediate Similarity	NPC292491
0.8214	Intermediate Similarity	NPC290690
0.8214	Intermediate Similarity	NPC470629
0.8214	Intermediate Similarity	NPC472739
0.8214	Intermediate Similarity	NPC17733
0.8205	Intermediate Similarity	NPC476811
0.8205	Intermediate Similarity	NPC106078
0.8205	Intermediate Similarity	NPC474433
0.8193	Intermediate Similarity	NPC187545
0.8193	Intermediate Similarity	NPC471737
0.8193	Intermediate Similarity	NPC98236
0.8193	Intermediate Similarity	NPC73038
0.8193	Intermediate Similarity	NPC34190
0.8193	Intermediate Similarity	NPC269396
0.8193	Intermediate Similarity	NPC325594
0.8193	Intermediate Similarity	NPC12774
0.8193	Intermediate Similarity	NPC2783
0.8182	Intermediate Similarity	NPC267753
0.8182	Intermediate Similarity	NPC97534
0.8182	Intermediate Similarity	NPC174964
0.8182	Intermediate Similarity	NPC273366
0.8182	Intermediate Similarity	NPC195155
0.8171	Intermediate Similarity	NPC171789
0.8171	Intermediate Similarity	NPC59453
0.8171	Intermediate Similarity	NPC221758
0.8161	Intermediate Similarity	NPC471207
0.8161	Intermediate Similarity	NPC209662
0.8158	Intermediate Similarity	NPC81759
0.8148	Intermediate Similarity	NPC163236
0.8148	Intermediate Similarity	NPC310989
0.8148	Intermediate Similarity	NPC477858
0.8148	Intermediate Similarity	NPC145143
0.8148	Intermediate Similarity	NPC73882
0.8148	Intermediate Similarity	NPC151519
0.814	Intermediate Similarity	NPC105189
0.814	Intermediate Similarity	NPC233455
0.814	Intermediate Similarity	NPC4036
0.814	Intermediate Similarity	NPC301244
0.814	Intermediate Similarity	NPC65120
0.814	Intermediate Similarity	NPC145067
0.814	Intermediate Similarity	NPC158030
0.814	Intermediate Similarity	NPC474525
0.8125	Intermediate Similarity	NPC2482
0.8125	Intermediate Similarity	NPC469637
0.8118	Intermediate Similarity	NPC59263
0.8118	Intermediate Similarity	NPC198664
0.8118	Intermediate Similarity	NPC270768
0.8118	Intermediate Similarity	NPC95246
0.8118	Intermediate Similarity	NPC474972
0.8118	Intermediate Similarity	NPC469319
0.8118	Intermediate Similarity	NPC293048
0.8118	Intermediate Similarity	NPC25906
0.8118	Intermediate Similarity	NPC229871
0.8118	Intermediate Similarity	NPC64872
0.8118	Intermediate Similarity	NPC234346
0.8118	Intermediate Similarity	NPC127689
0.8118	Intermediate Similarity	NPC143232
0.8118	Intermediate Similarity	NPC274330
0.8118	Intermediate Similarity	NPC121798
0.8118	Intermediate Similarity	NPC263393
0.8118	Intermediate Similarity	NPC130520
0.8118	Intermediate Similarity	NPC290972
0.8118	Intermediate Similarity	NPC61543
0.8118	Intermediate Similarity	NPC470588
0.8118	Intermediate Similarity	NPC225585
0.8118	Intermediate Similarity	NPC161751
0.8101	Intermediate Similarity	NPC476810
0.8095	Intermediate Similarity	NPC165895
0.8095	Intermediate Similarity	NPC269360
0.8095	Intermediate Similarity	NPC153604
0.8095	Intermediate Similarity	NPC174619
0.8095	Intermediate Similarity	NPC264005
0.8095	Intermediate Similarity	NPC142361
0.8095	Intermediate Similarity	NPC71507
0.8095	Intermediate Similarity	NPC469317
0.8095	Intermediate Similarity	NPC475740
0.8095	Intermediate Similarity	NPC469314
0.8095	Intermediate Similarity	NPC298904
0.8095	Intermediate Similarity	NPC472497
0.8095	Intermediate Similarity	NPC58063
0.8095	Intermediate Similarity	NPC259009
0.8095	Intermediate Similarity	NPC241875
0.8095	Intermediate Similarity	NPC33768
0.8095	Intermediate Similarity	NPC474684
0.8095	Intermediate Similarity	NPC472495
0.8077	Intermediate Similarity	NPC198473
0.8077	Intermediate Similarity	NPC475742
0.8077	Intermediate Similarity	NPC472487
0.8077	Intermediate Similarity	NPC5767
0.8077	Intermediate Similarity	NPC472486
0.8077	Intermediate Similarity	NPC108840
0.8072	Intermediate Similarity	NPC102292
0.8072	Intermediate Similarity	NPC274724
0.8052	Intermediate Similarity	NPC254340
0.8052	Intermediate Similarity	NPC130011
0.8052	Intermediate Similarity	NPC255168
0.8049	Intermediate Similarity	NPC471037
0.8046	Intermediate Similarity	NPC214756
0.8046	Intermediate Similarity	NPC295643
0.8046	Intermediate Similarity	NPC272075
0.8046	Intermediate Similarity	NPC12722
0.8025	Intermediate Similarity	NPC103754
0.8025	Intermediate Similarity	NPC48673
0.8025	Intermediate Similarity	NPC20096

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 NPC472746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	2114
0.2-0.3	4071
0.3-0.4	1940
0.4-0.5	438
0.5-0.6	194
0.6-0.7	159
0.7-0.8	53
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8293	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3618	Phase 1
0.8171	Intermediate Similarity	NPD4786	Approved
0.8148	Intermediate Similarity	NPD3667	Approved
0.814	Intermediate Similarity	NPD7515	Phase 2
0.814	Intermediate Similarity	NPD6079	Approved
0.8118	Intermediate Similarity	NPD5328	Approved
0.7949	Intermediate Similarity	NPD3703	Phase 2
0.7895	Intermediate Similarity	NPD4245	Approved
0.7895	Intermediate Similarity	NPD4244	Approved
0.7848	Intermediate Similarity	NPD6117	Approved
0.7831	Intermediate Similarity	NPD4788	Approved
0.7821	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3698	Phase 2
0.7753	Intermediate Similarity	NPD7748	Approved
0.775	Intermediate Similarity	NPD6116	Phase 1
0.7738	Intermediate Similarity	NPD3665	Phase 1
0.7738	Intermediate Similarity	NPD3666	Approved
0.7738	Intermediate Similarity	NPD3133	Approved
0.7662	Intermediate Similarity	NPD4789	Approved
0.7654	Intermediate Similarity	NPD6114	Approved
0.7654	Intermediate Similarity	NPD6115	Approved
0.7654	Intermediate Similarity	NPD6118	Approved
0.7654	Intermediate Similarity	NPD6697	Approved
0.764	Intermediate Similarity	NPD4202	Approved
0.7632	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5360	Phase 3
0.7582	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5222	Approved
0.7582	Intermediate Similarity	NPD5221	Approved
0.7561	Intermediate Similarity	NPD7645	Phase 2
0.7528	Intermediate Similarity	NPD8035	Phase 2
0.7528	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.747	Intermediate Similarity	NPD7525	Registered
0.7467	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3671	Phase 1
0.7391	Intermediate Similarity	NPD4697	Phase 3
0.734	Intermediate Similarity	NPD5285	Approved
0.734	Intermediate Similarity	NPD5286	Approved
0.734	Intermediate Similarity	NPD4696	Approved
0.7326	Intermediate Similarity	NPD3668	Phase 3
0.7312	Intermediate Similarity	NPD4755	Approved
0.7263	Intermediate Similarity	NPD5223	Approved
0.7253	Intermediate Similarity	NPD6399	Phase 3
0.7188	Intermediate Similarity	NPD5211	Phase 2
0.7188	Intermediate Similarity	NPD5225	Approved
0.7188	Intermediate Similarity	NPD5226	Approved
0.7188	Intermediate Similarity	NPD4633	Approved
0.7188	Intermediate Similarity	NPD5224	Approved
0.7174	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7900	Approved
0.7159	Intermediate Similarity	NPD5279	Phase 3
0.7159	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD4224	Phase 2
0.7125	Intermediate Similarity	NPD4758	Discontinued
0.7113	Intermediate Similarity	NPD5175	Approved
0.7113	Intermediate Similarity	NPD5174	Approved
0.7111	Intermediate Similarity	NPD4753	Phase 2
0.7093	Intermediate Similarity	NPD4221	Approved
0.7093	Intermediate Similarity	NPD4223	Phase 3
0.7073	Intermediate Similarity	NPD7339	Approved
0.7073	Intermediate Similarity	NPD6942	Approved
0.7059	Intermediate Similarity	NPD4695	Discontinued
0.7053	Intermediate Similarity	NPD7638	Approved
0.7045	Intermediate Similarity	NPD5329	Approved
0.7041	Intermediate Similarity	NPD5141	Approved
0.7024	Intermediate Similarity	NPD3617	Approved
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6881	Approved
0.7	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7639	Approved
0.6979	Remote Similarity	NPD7640	Approved
0.697	Remote Similarity	NPD6675	Approved
0.697	Remote Similarity	NPD7128	Approved
0.697	Remote Similarity	NPD6402	Approved
0.697	Remote Similarity	NPD5739	Approved
0.6966	Remote Similarity	NPD7146	Approved
0.6966	Remote Similarity	NPD7334	Approved
0.6966	Remote Similarity	NPD6684	Approved
0.6966	Remote Similarity	NPD4623	Approved
0.6966	Remote Similarity	NPD5330	Approved
0.6966	Remote Similarity	NPD7521	Approved
0.6966	Remote Similarity	NPD6409	Approved
0.6966	Remote Similarity	NPD4519	Discontinued
0.6939	Remote Similarity	NPD4754	Approved
0.6932	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4629	Approved
0.6915	Remote Similarity	NPD5210	Approved
0.6914	Remote Similarity	NPD6081	Approved
0.6914	Remote Similarity	NPD5777	Approved
0.69	Remote Similarity	NPD5697	Approved
0.6889	Remote Similarity	NPD3573	Approved
0.6875	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6883	Approved
0.6863	Remote Similarity	NPD7102	Approved
0.6863	Remote Similarity	NPD7290	Approved
0.6832	Remote Similarity	NPD4729	Approved
0.6832	Remote Similarity	NPD6011	Approved
0.6832	Remote Similarity	NPD4730	Approved
0.6832	Remote Similarity	NPD7320	Approved
0.6832	Remote Similarity	NPD5168	Approved
0.6824	Remote Similarity	NPD5364	Discontinued
0.6813	Remote Similarity	NPD6903	Approved
0.68	Remote Similarity	NPD4768	Approved
0.68	Remote Similarity	NPD4767	Approved
0.6796	Remote Similarity	NPD6847	Approved
0.6796	Remote Similarity	NPD6650	Approved
0.6796	Remote Similarity	NPD6617	Approved
0.6796	Remote Similarity	NPD8130	Phase 1
0.6796	Remote Similarity	NPD6869	Approved
0.6796	Remote Similarity	NPD6649	Approved
0.6778	Remote Similarity	NPD4688	Approved
0.6778	Remote Similarity	NPD5690	Phase 2
0.6778	Remote Similarity	NPD4690	Approved
0.6778	Remote Similarity	NPD4138	Approved
0.6778	Remote Similarity	NPD5205	Approved
0.6778	Remote Similarity	NPD4693	Phase 3
0.6778	Remote Similarity	NPD4689	Approved
0.6774	Remote Similarity	NPD6411	Approved
0.6771	Remote Similarity	NPD6084	Phase 2
0.6771	Remote Similarity	NPD6083	Phase 2
0.6765	Remote Similarity	NPD6373	Approved
0.6765	Remote Similarity	NPD6014	Approved
0.6765	Remote Similarity	NPD6012	Approved
0.6765	Remote Similarity	NPD6013	Approved
0.6765	Remote Similarity	NPD6372	Approved
0.6733	Remote Similarity	NPD5701	Approved
0.6731	Remote Similarity	NPD6882	Approved
0.6731	Remote Similarity	NPD8297	Approved
0.6699	Remote Similarity	NPD5248	Approved
0.6699	Remote Similarity	NPD5249	Phase 3
0.6699	Remote Similarity	NPD5247	Approved
0.6699	Remote Similarity	NPD5250	Approved
0.6699	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5251	Approved
0.6699	Remote Similarity	NPD4634	Approved
0.6699	Remote Similarity	NPD5135	Approved
0.6699	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5128	Approved
0.6635	Remote Similarity	NPD5215	Approved
0.6635	Remote Similarity	NPD5127	Approved
0.6635	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5216	Approved
0.6635	Remote Similarity	NPD5217	Approved
0.663	Remote Similarity	NPD6672	Approved
0.663	Remote Similarity	NPD5737	Approved
0.6628	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4694	Approved
0.6593	Remote Similarity	NPD5280	Approved
0.6591	Remote Similarity	NPD4139	Approved
0.6591	Remote Similarity	NPD4692	Approved
0.6585	Remote Similarity	NPD4787	Phase 1
0.6559	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6101	Approved
0.6552	Remote Similarity	NPD4195	Approved
0.6548	Remote Similarity	NPD6926	Approved
0.6548	Remote Similarity	NPD6924	Approved
0.6542	Remote Similarity	NPD6868	Approved
0.6531	Remote Similarity	NPD5290	Discontinued
0.6509	Remote Similarity	NPD4632	Approved
0.6506	Remote Similarity	NPD7151	Approved
0.6506	Remote Similarity	NPD7150	Approved
0.6506	Remote Similarity	NPD7152	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.6495	Remote Similarity	NPD7614	Phase 1
0.6484	Remote Similarity	NPD1694	Approved
0.6481	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD8264	Approved
0.6471	Remote Similarity	NPD3702	Approved
0.6463	Remote Similarity	NPD4137	Phase 3
0.6449	Remote Similarity	NPD5167	Approved
0.6442	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6335	Approved
0.6421	Remote Similarity	NPD5284	Approved
0.6421	Remote Similarity	NPD5281	Approved
0.6413	Remote Similarity	NPD6098	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.6395	Remote Similarity	NPD6933	Approved
0.6392	Remote Similarity	NPD5695	Phase 3
0.6392	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7144	Approved
0.6386	Remote Similarity	NPD4691	Approved
0.6386	Remote Similarity	NPD4747	Approved
0.6386	Remote Similarity	NPD7143	Approved
0.6364	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD7100	Approved
0.6353	Remote Similarity	NPD4785	Approved
0.6353	Remote Similarity	NPD4784	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