NPASS Compound

Structure

NPC472255 OpenBabel07101719142D 23 24 0 0 1 0 0 0 0 0999 V2000 2.4972 4.2554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 5.1214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1140 0.3251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2602 -3.2191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3632 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4972 2.5233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 3.3894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1273 -1.4568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4255 -2.1692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 1.6573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2658 -1.8565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4972 4.2554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6667 -0.5692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 -2.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 -1.7219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5605 -0.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6802 -0.7331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9972 -0.0747 0.0000 C 0 0 2 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 1.4972 0.7913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5494 -0.7519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3653 0.9309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3632 1.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 2 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 14 15 1 0 0 0 0 15 9 1 6 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 1 0 0 0 17 13 1 1 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 19 22 1 6 0 0 0 20 5 1 1 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	355.825
LogP:	4.331
LogD:	3.625
LogS:	-3.315
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.696
Synthetic Accessibility Score:	4.816
Fsp3:	0.7
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:	-4.741
MDCK Permeability:	1.3867412235413212e-05
Pgp-inhibitor:	0.591
Pgp-substrate:	0.593
Human Intestinal Absorption (HIA):	0.106
20% Bioavailability (F20%):	0.924
30% Bioavailability (F30%):	0.55

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.746
Plasma Protein Binding (PPB):	84.8357925415039%
Volume Distribution (VD):	1.525
Pgp-substrate:	10.84106731414795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	15.028
Half-life (T1/2):	0.49

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.679
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.249
Carcinogencity:	0.325
Eye Corrosion:	0.07
Eye Irritation:	0.417
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC472255

Natural Product ID:	NPC472255
*Common Name:**	MVFPHQGMZUMNFE-GTYQWKCWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MVFPHQGMZUMNFE-GTYQWKCWSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-12(2)7-6-10-20(5,23)18-16(21)11-14(4)15-9-8-13(3)17(15)19(18)22/h7-8,15-19,21-23H,4,6,9-11H2,1-3,5H3/t15-,16-,17+,18+,19-,20-/m0/s1
SMILES:	CC1=CCC2C1C(C(C(CC2=C)O)C(C)(CCC=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3355407
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003550] Pachydictyane and cneorubin 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
NPO32773	dictyota plectens	Species	Dictyotaceae	Eukaryota	n.a.	China	n.a.	PMID[25495797]

☑ 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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	CC50	>	60000.0	nM	PMID[542485]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[542485]
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[542485]

☑ 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 NPC472255 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	170
0.1-0.2	1924
0.2-0.3	11005
0.3-0.4	15330
0.4-0.5	8267
0.5-0.6	4998
0.6-0.7	898
0.7-0.8	91
0.8-0.85	5
0.85-0.9	4
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472253
0.9839	High Similarity	NPC272125
0.9538	High Similarity	NPC470041
0.9355	High Similarity	NPC279200
0.8889	High Similarity	NPC274704
0.8462	Intermediate Similarity	NPC211291
0.8462	Intermediate Similarity	NPC133368
0.8413	Intermediate Similarity	NPC475830
0.8382	Intermediate Similarity	NPC224532
0.8286	Intermediate Similarity	NPC471662
0.8209	Intermediate Similarity	NPC238352
0.8209	Intermediate Similarity	NPC477009
0.8209	Intermediate Similarity	NPC19569
0.8116	Intermediate Similarity	NPC167527
0.8095	Intermediate Similarity	NPC274396
0.806	Intermediate Similarity	NPC309300
0.8056	Intermediate Similarity	NPC329090
0.8056	Intermediate Similarity	NPC27395
0.8056	Intermediate Similarity	NPC471659
0.8	Intermediate Similarity	NPC5698
0.8	Intermediate Similarity	NPC475931
0.8	Intermediate Similarity	NPC122239
0.7973	Intermediate Similarity	NPC31037
0.7971	Intermediate Similarity	NPC136813
0.7969	Intermediate Similarity	NPC278550
0.7945	Intermediate Similarity	NPC328104
0.7945	Intermediate Similarity	NPC319090
0.7887	Intermediate Similarity	NPC471781
0.7879	Intermediate Similarity	NPC323153
0.7846	Intermediate Similarity	NPC10017
0.7838	Intermediate Similarity	NPC315261
0.7761	Intermediate Similarity	NPC210346
0.7746	Intermediate Similarity	NPC144647
0.7733	Intermediate Similarity	NPC198968
0.7733	Intermediate Similarity	NPC318495
0.7733	Intermediate Similarity	NPC155986
0.7727	Intermediate Similarity	NPC469321
0.7714	Intermediate Similarity	NPC477791
0.7703	Intermediate Similarity	NPC113639
0.7692	Intermediate Similarity	NPC52012
0.7681	Intermediate Similarity	NPC261782
0.7681	Intermediate Similarity	NPC205618
0.7681	Intermediate Similarity	NPC469326
0.7671	Intermediate Similarity	NPC474140
0.7671	Intermediate Similarity	NPC476709
0.7662	Intermediate Similarity	NPC324772
0.7619	Intermediate Similarity	NPC192962
0.7612	Intermediate Similarity	NPC252809
0.7612	Intermediate Similarity	NPC471081
0.76	Intermediate Similarity	NPC310643
0.76	Intermediate Similarity	NPC107059
0.76	Intermediate Similarity	NPC471658
0.76	Intermediate Similarity	NPC321381
0.76	Intermediate Similarity	NPC321016
0.7576	Intermediate Similarity	NPC181872
0.7576	Intermediate Similarity	NPC226848
0.7571	Intermediate Similarity	NPC267027
0.7571	Intermediate Similarity	NPC469328
0.7564	Intermediate Similarity	NPC320525
0.7536	Intermediate Similarity	NPC140233
0.7536	Intermediate Similarity	NPC225415
0.7536	Intermediate Similarity	NPC300593
0.7536	Intermediate Similarity	NPC290367
0.7536	Intermediate Similarity	NPC287744
0.7534	Intermediate Similarity	NPC471660
0.7534	Intermediate Similarity	NPC41886
0.7532	Intermediate Similarity	NPC328714
0.75	Intermediate Similarity	NPC475251
0.75	Intermediate Similarity	NPC63111
0.75	Intermediate Similarity	NPC329989
0.75	Intermediate Similarity	NPC167272
0.75	Intermediate Similarity	NPC239373
0.75	Intermediate Similarity	NPC269877
0.75	Intermediate Similarity	NPC471454
0.75	Intermediate Similarity	NPC217570
0.75	Intermediate Similarity	NPC90115
0.7467	Intermediate Similarity	NPC285893
0.7467	Intermediate Similarity	NPC304309
0.7467	Intermediate Similarity	NPC162742
0.7467	Intermediate Similarity	NPC136188
0.7467	Intermediate Similarity	NPC22105
0.7467	Intermediate Similarity	NPC230301
0.7467	Intermediate Similarity	NPC23231
0.7467	Intermediate Similarity	NPC288035
0.7467	Intermediate Similarity	NPC134847
0.7467	Intermediate Similarity	NPC28657
0.7467	Intermediate Similarity	NPC60818
0.7465	Intermediate Similarity	NPC73603
0.7436	Intermediate Similarity	NPC209944
0.7436	Intermediate Similarity	NPC164840
0.7436	Intermediate Similarity	NPC241290
0.7429	Intermediate Similarity	NPC471200
0.7429	Intermediate Similarity	NPC308844
0.7419	Intermediate Similarity	NPC329773
0.7403	Intermediate Similarity	NPC473943
0.7403	Intermediate Similarity	NPC477522
0.7403	Intermediate Similarity	NPC87604
0.7403	Intermediate Similarity	NPC474216
0.7403	Intermediate Similarity	NPC285761
0.7403	Intermediate Similarity	NPC275910
0.7397	Intermediate Similarity	NPC9161
0.7397	Intermediate Similarity	NPC49422
0.7391	Intermediate Similarity	NPC474480
0.7391	Intermediate Similarity	NPC473508
0.7385	Intermediate Similarity	NPC281590
0.7375	Intermediate Similarity	NPC320548
0.7368	Intermediate Similarity	NPC240604
0.7368	Intermediate Similarity	NPC113733
0.7368	Intermediate Similarity	NPC300324
0.7368	Intermediate Similarity	NPC126969
0.7361	Intermediate Similarity	NPC305698
0.7361	Intermediate Similarity	NPC208999
0.7361	Intermediate Similarity	NPC160209
0.7353	Intermediate Similarity	NPC66020
0.7353	Intermediate Similarity	NPC99487
0.7342	Intermediate Similarity	NPC264245
0.7342	Intermediate Similarity	NPC471661
0.7342	Intermediate Similarity	NPC470383
0.7342	Intermediate Similarity	NPC47761
0.7333	Intermediate Similarity	NPC471525
0.7333	Intermediate Similarity	NPC471797
0.7324	Intermediate Similarity	NPC162309
0.7313	Intermediate Similarity	NPC155025
0.7308	Intermediate Similarity	NPC28862
0.7308	Intermediate Similarity	NPC273410
0.7308	Intermediate Similarity	NPC80530
0.7308	Intermediate Similarity	NPC84694
0.7308	Intermediate Similarity	NPC47982
0.7308	Intermediate Similarity	NPC476701
0.7308	Intermediate Similarity	NPC472463
0.7308	Intermediate Similarity	NPC143182
0.7308	Intermediate Similarity	NPC81306
0.7308	Intermediate Similarity	NPC109546
0.7297	Intermediate Similarity	NPC242001
0.7297	Intermediate Similarity	NPC167706
0.7286	Intermediate Similarity	NPC219940
0.7284	Intermediate Similarity	NPC474493
0.7284	Intermediate Similarity	NPC205845
0.7273	Intermediate Similarity	NPC476703
0.7273	Intermediate Similarity	NPC476439
0.7273	Intermediate Similarity	NPC214570
0.7273	Intermediate Similarity	NPC34019
0.726	Intermediate Similarity	NPC304690
0.726	Intermediate Similarity	NPC16964
0.726	Intermediate Similarity	NPC74722
0.725	Intermediate Similarity	NPC49964
0.725	Intermediate Similarity	NPC248886
0.725	Intermediate Similarity	NPC472465
0.725	Intermediate Similarity	NPC101462
0.725	Intermediate Similarity	NPC30166
0.7246	Intermediate Similarity	NPC225342
0.7237	Intermediate Similarity	NPC12696
0.7237	Intermediate Similarity	NPC141071
0.7237	Intermediate Similarity	NPC471723
0.7237	Intermediate Similarity	NPC257347
0.7222	Intermediate Similarity	NPC114651
0.7222	Intermediate Similarity	NPC259299
0.7215	Intermediate Similarity	NPC322313
0.7215	Intermediate Similarity	NPC236237
0.7215	Intermediate Similarity	NPC26117
0.7215	Intermediate Similarity	NPC102253
0.7215	Intermediate Similarity	NPC234193
0.7215	Intermediate Similarity	NPC13554
0.7206	Intermediate Similarity	NPC310228
0.7206	Intermediate Similarity	NPC52431
0.72	Intermediate Similarity	NPC220939
0.72	Intermediate Similarity	NPC234527
0.72	Intermediate Similarity	NPC265485
0.72	Intermediate Similarity	NPC329763
0.72	Intermediate Similarity	NPC471799
0.72	Intermediate Similarity	NPC14352
0.7195	Intermediate Similarity	NPC474349
0.7195	Intermediate Similarity	NPC474189
0.7183	Intermediate Similarity	NPC61503
0.7179	Intermediate Similarity	NPC307965
0.7179	Intermediate Similarity	NPC244385
0.7179	Intermediate Similarity	NPC6978
0.7179	Intermediate Similarity	NPC477514
0.7179	Intermediate Similarity	NPC76931
0.7179	Intermediate Similarity	NPC312328
0.7179	Intermediate Similarity	NPC318136
0.7179	Intermediate Similarity	NPC18603
0.7179	Intermediate Similarity	NPC138621
0.7179	Intermediate Similarity	NPC167037
0.7162	Intermediate Similarity	NPC145498
0.7162	Intermediate Similarity	NPC280256
0.7162	Intermediate Similarity	NPC34834
0.716	Intermediate Similarity	NPC475789
0.716	Intermediate Similarity	NPC470384
0.716	Intermediate Similarity	NPC474634
0.7143	Intermediate Similarity	NPC189883
0.7143	Intermediate Similarity	NPC46160
0.7143	Intermediate Similarity	NPC129165
0.7143	Intermediate Similarity	NPC202642
0.7143	Intermediate Similarity	NPC96319
0.7143	Intermediate Similarity	NPC247325
0.7143	Intermediate Similarity	NPC476317
0.7143	Intermediate Similarity	NPC470362
0.7143	Intermediate Similarity	NPC265588
0.7143	Intermediate Similarity	NPC134330

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 NPC472255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2600
0.2-0.3	4139
0.3-0.4	1643
0.4-0.5	424
0.5-0.6	136
0.6-0.7	44
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8056	Intermediate Similarity	NPD6926	Approved
0.8056	Intermediate Similarity	NPD6924	Approved
0.7838	Intermediate Similarity	NPD6933	Approved
0.7662	Intermediate Similarity	NPD7509	Discontinued
0.7662	Intermediate Similarity	NPD6931	Approved
0.7662	Intermediate Similarity	NPD6930	Phase 2
0.7532	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD6922	Approved
0.75	Intermediate Similarity	NPD6932	Approved
0.75	Intermediate Similarity	NPD6923	Approved
0.7467	Intermediate Similarity	NPD6942	Approved
0.7467	Intermediate Similarity	NPD7339	Approved
0.7436	Intermediate Similarity	NPD7332	Phase 2
0.7403	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7144	Approved
0.7397	Intermediate Similarity	NPD7143	Approved
0.7375	Intermediate Similarity	NPD6695	Phase 3
0.7342	Intermediate Similarity	NPD6898	Phase 1
0.7308	Intermediate Similarity	NPD6683	Phase 2
0.7297	Intermediate Similarity	NPD7152	Approved
0.7297	Intermediate Similarity	NPD7150	Approved
0.7297	Intermediate Similarity	NPD7151	Approved
0.7284	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5776	Phase 2
0.7273	Intermediate Similarity	NPD6925	Approved
0.7215	Intermediate Similarity	NPD7514	Phase 3
0.7215	Intermediate Similarity	NPD7525	Registered
0.7195	Intermediate Similarity	NPD6893	Approved
0.7179	Intermediate Similarity	NPD7145	Approved
0.7143	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7524	Approved
0.7024	Intermediate Similarity	NPD7750	Discontinued
0.7	Intermediate Similarity	NPD4821	Approved
0.7	Intermediate Similarity	NPD368	Approved
0.7	Intermediate Similarity	NPD4822	Approved
0.7	Intermediate Similarity	NPD4820	Approved
0.7	Intermediate Similarity	NPD4819	Approved
0.6951	Remote Similarity	NPD5362	Discontinued
0.6914	Remote Similarity	NPD6902	Approved
0.6883	Remote Similarity	NPD4785	Approved
0.6883	Remote Similarity	NPD4784	Approved
0.6867	Remote Similarity	NPD4786	Approved
0.6842	Remote Similarity	NPD4243	Approved
0.675	Remote Similarity	NPD4268	Approved
0.675	Remote Similarity	NPD4271	Approved
0.6747	Remote Similarity	NPD7154	Phase 3
0.6747	Remote Similarity	NPD5331	Approved
0.6747	Remote Similarity	NPD5332	Approved
0.6707	Remote Similarity	NPD4790	Discontinued
0.6707	Remote Similarity	NPD5369	Approved
0.6705	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD7645	Phase 2
0.6628	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3667	Approved
0.6618	Remote Similarity	NPD342	Phase 1
0.6585	Remote Similarity	NPD4748	Discontinued
0.6585	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5368	Approved
0.6582	Remote Similarity	NPD8264	Approved
0.6543	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4269	Approved
0.6429	Remote Similarity	NPD6435	Approved
0.6429	Remote Similarity	NPD4270	Approved
0.6404	Remote Similarity	NPD7136	Phase 2
0.6395	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4190	Phase 3
0.6375	Remote Similarity	NPD5275	Approved
0.6322	Remote Similarity	NPD5279	Phase 3
0.6292	Remote Similarity	NPD4753	Phase 2
0.6292	Remote Similarity	NPD1695	Approved
0.6292	Remote Similarity	NPD5328	Approved
0.6279	Remote Similarity	NPD3665	Phase 1
0.6279	Remote Similarity	NPD3666	Approved
0.6279	Remote Similarity	NPD3133	Approved
0.6265	Remote Similarity	NPD4195	Approved
0.6207	Remote Similarity	NPD5363	Approved
0.619	Remote Similarity	NPD4252	Approved
0.6184	Remote Similarity	NPD7331	Phase 2
0.6154	Remote Similarity	NPD7637	Suspended
0.6154	Remote Similarity	NPD6079	Approved
0.6136	Remote Similarity	NPD5786	Approved
0.6136	Remote Similarity	NPD3618	Phase 1
0.6129	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4732	Discontinued
0.6111	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6101	Approved
0.6087	Remote Similarity	NPD6399	Phase 3
0.6087	Remote Similarity	NPD4202	Approved
0.6067	Remote Similarity	NPD4251	Approved
0.6067	Remote Similarity	NPD4250	Approved
0.6053	Remote Similarity	NPD7341	Phase 2
0.6047	Remote Similarity	NPD4221	Approved
0.6047	Remote Similarity	NPD4223	Phase 3
0.6023	Remote Similarity	NPD5329	Approved
0.6022	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4265	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD4755	Approved
0.598	Remote Similarity	NPD6371	Approved
0.5978	Remote Similarity	NPD6411	Approved
0.5977	Remote Similarity	NPD4788	Approved
0.5957	Remote Similarity	NPD5210	Approved
0.5957	Remote Similarity	NPD4629	Approved
0.5955	Remote Similarity	NPD4249	Approved
0.5914	Remote Similarity	NPD5778	Approved
0.5914	Remote Similarity	NPD5779	Approved
0.5909	Remote Similarity	NPD4197	Approved
0.5909	Remote Similarity	NPD3668	Phase 3
0.5904	Remote Similarity	NPD1346	Approved
0.5876	Remote Similarity	NPD4700	Approved
0.5876	Remote Similarity	NPD5286	Approved
0.5876	Remote Similarity	NPD4696	Approved
0.5876	Remote Similarity	NPD5285	Approved
0.587	Remote Similarity	NPD5785	Approved
0.587	Remote Similarity	NPD7838	Discovery
0.5844	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4518	Approved
0.5789	Remote Similarity	NPD5695	Phase 3
0.5778	Remote Similarity	NPD5280	Approved
0.5778	Remote Similarity	NPD4138	Approved
0.5778	Remote Similarity	NPD4688	Approved
0.5778	Remote Similarity	NPD5205	Approved
0.5778	Remote Similarity	NPD4689	Approved
0.5778	Remote Similarity	NPD4693	Phase 3
0.5778	Remote Similarity	NPD4690	Approved
0.5778	Remote Similarity	NPD5690	Phase 2
0.5778	Remote Similarity	NPD4694	Approved
0.5761	Remote Similarity	NPD6051	Approved
0.5758	Remote Similarity	NPD5226	Approved
0.5758	Remote Similarity	NPD5211	Phase 2
0.5758	Remote Similarity	NPD4633	Approved
0.5758	Remote Similarity	NPD5224	Approved
0.5758	Remote Similarity	NPD5225	Approved
0.575	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.575	Remote Similarity	NPD1082	Approved
0.5743	Remote Similarity	NPD6675	Approved
0.5743	Remote Similarity	NPD6402	Approved
0.5743	Remote Similarity	NPD5739	Approved
0.5743	Remote Similarity	NPD6640	Phase 3
0.5743	Remote Similarity	NPD7128	Approved
0.5733	Remote Similarity	NPD1145	Discontinued
0.573	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.573	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5221	Approved
0.5729	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4697	Phase 3
0.5729	Remote Similarity	NPD5222	Approved
0.5714	Remote Similarity	NPD3197	Phase 1
0.5714	Remote Similarity	NPD6053	Discontinued
0.57	Remote Similarity	NPD5175	Approved
0.57	Remote Similarity	NPD5174	Approved
0.5699	Remote Similarity	NPD3168	Discontinued
0.5699	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD6698	Approved
0.5699	Remote Similarity	NPD46	Approved
0.5682	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD385	Approved
0.5672	Remote Similarity	NPD384	Approved
0.567	Remote Similarity	NPD5173	Approved
0.5667	Remote Similarity	NPD1696	Phase 3
0.5657	Remote Similarity	NPD5223	Approved
0.5657	Remote Similarity	NPD5344	Discontinued
0.5652	Remote Similarity	NPD4722	Approved
0.5652	Remote Similarity	NPD4723	Approved
0.5644	Remote Similarity	NPD5141	Approved
0.5638	Remote Similarity	NPD7515	Phase 2
0.5638	Remote Similarity	NPD7983	Approved
0.5632	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD4695	Discontinued
0.5631	Remote Similarity	NPD6899	Approved
0.5631	Remote Similarity	NPD6881	Approved
0.5631	Remote Similarity	NPD7320	Approved
0.5616	Remote Similarity	NPD4219	Approved
0.5612	Remote Similarity	NPD5696	Approved
0.5612	Remote Similarity	NPD7638	Approved
0.5612	Remote Similarity	NPD4225	Approved
0.5604	Remote Similarity	NPD4519	Discontinued
0.5604	Remote Similarity	NPD7146	Approved
0.5604	Remote Similarity	NPD5330	Approved
0.5604	Remote Similarity	NPD7521	Approved
0.5604	Remote Similarity	NPD7334	Approved
0.5604	Remote Similarity	NPD4623	Approved
0.5604	Remote Similarity	NPD6684	Approved
0.5604	Remote Similarity	NPD6409	Approved
0.56	Remote Similarity	NPD3198	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