NPASS Compound

Structure

NPC272125 OpenBabel07101719242D 22 23 0 0 1 0 0 0 0 0999 V2000 3.9972 -1.8068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4972 -0.9408 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 -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 2.9972 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9972 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4972 0.7913 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 1.2658 -1.8565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4972 -0.9408 0.0000 C 0 0 0 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 -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 2 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 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 1 12 1 0 0 0 0 2 12 1 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 12 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 13 3 1 6 0 0 0 15 16 1 0 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 6 0 0 0 18 14 1 1 0 0 0 18 20 1 0 0 0 0 19 13 1 6 0 0 0 19 20 1 0 0 0 0 20 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	347.034
LogP:	5.51
LogD:	4.535
LogS:	-3.939
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	4.699
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:	-4.655
MDCK Permeability:	1.2637930922210217e-05
Pgp-inhibitor:	0.558
Pgp-substrate:	0.112
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.859
30% Bioavailability (F30%):	0.521

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	94.2267837524414%
Volume Distribution (VD):	1.696
Pgp-substrate:	5.425768852233887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.323
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.572
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	13.734
Half-life (T1/2):	0.346

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.714
Drug-inuced Liver Injury (DILI):	0.221
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.216
Carcinogencity:	0.096
Eye Corrosion:	0.01
Eye Irritation:	0.128
Respiratory Toxicity:	0.164

Download Data

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

Natural Product: NPC272125

Natural Product ID:	NPC272125
*Common Name:**	8Beta-Hydroxypachydictyol A
IUPAC Name:	(3aS,4S,5R,6R,8aR)-3-methyl-5-[(2R)-6-methylhept-5-en-2-yl]-8-methylidene-3a,4,5,6,7,8a-hexahydro-1H-azulene-4,6-diol
Synonyms:	8Beta-Hydroxypachydictyol A
Standard InCHIKey:	BKGLGOGPWGBWFY-AJTFGXLRSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-12(2)7-6-8-13(3)19-17(21)11-15(5)16-10-9-14(4)18(16)20(19)22/h7,9,13,16-22H,5-6,8,10-11H2,1-4H3/t13-,16+,17-,18-,19-,20+/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@@H]1[C@@H](CC(=C)[C@@H]2CC=C(C)[C@H]2[C@@H]1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1652220
PubChem CID:	53325968
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
NPO32968	dictoyota dichotoma	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21130542]
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
IC50	6
Others	4

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	1
Others	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	81.2	ug.mL-1	PMID[520994]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	72.3	ug.mL-1	PMID[520994]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	68.2	ug.mL-1	PMID[520994]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	60000.0	nM	PMID[520995]
NPT27	Others	Unspecified		IC50	=	62.6	ug.mL-1	PMID[520994]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	60.9	%	PMID[520994]
NPT632	Tissue	Brain	Rattus norvegicus	Inhibition	=	61.65	%	PMID[520994]
NPT27	Others	Unspecified		Activity	=	1.1	%	PMID[520994]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[520995]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	26100.0	nM	PMID[520995]

☑ 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 NPC272125 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	163
0.1-0.2	1867
0.2-0.3	11103
0.3-0.4	15384
0.4-0.5	8276
0.5-0.6	4895
0.6-0.7	914
0.7-0.8	81
0.8-0.85	4
0.85-0.9	5
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC472255
0.9839	High Similarity	NPC472253
0.9508	High Similarity	NPC279200
0.9385	High Similarity	NPC470041
0.9032	High Similarity	NPC274704
0.8594	High Similarity	NPC211291
0.8594	High Similarity	NPC133368
0.8548	High Similarity	NPC475830
0.8406	Intermediate Similarity	NPC471662
0.8333	Intermediate Similarity	NPC477009
0.8333	Intermediate Similarity	NPC238352
0.8333	Intermediate Similarity	NPC19569
0.8235	Intermediate Similarity	NPC224532
0.8235	Intermediate Similarity	NPC167527
0.8182	Intermediate Similarity	NPC309300
0.8125	Intermediate Similarity	NPC122239
0.7969	Intermediate Similarity	NPC10017
0.7937	Intermediate Similarity	NPC274396
0.7917	Intermediate Similarity	NPC471659
0.7917	Intermediate Similarity	NPC27395
0.7917	Intermediate Similarity	NPC329090
0.7846	Intermediate Similarity	NPC5698
0.7846	Intermediate Similarity	NPC475931
0.7838	Intermediate Similarity	NPC31037
0.7826	Intermediate Similarity	NPC136813
0.7826	Intermediate Similarity	NPC477791
0.7812	Intermediate Similarity	NPC278550
0.7808	Intermediate Similarity	NPC319090
0.7808	Intermediate Similarity	NPC328104
0.7778	Intermediate Similarity	NPC474140
0.7746	Intermediate Similarity	NPC471781
0.7727	Intermediate Similarity	NPC471081
0.7727	Intermediate Similarity	NPC323153
0.7703	Intermediate Similarity	NPC321381
0.7703	Intermediate Similarity	NPC315261
0.7703	Intermediate Similarity	NPC107059
0.7703	Intermediate Similarity	NPC321016
0.7692	Intermediate Similarity	NPC226848
0.7647	Intermediate Similarity	NPC225415
0.7647	Intermediate Similarity	NPC290367
0.7612	Intermediate Similarity	NPC210346
0.7606	Intermediate Similarity	NPC167272
0.7606	Intermediate Similarity	NPC217570
0.7606	Intermediate Similarity	NPC144647
0.7606	Intermediate Similarity	NPC269877
0.7606	Intermediate Similarity	NPC90115
0.76	Intermediate Similarity	NPC198968
0.76	Intermediate Similarity	NPC155986
0.76	Intermediate Similarity	NPC318495
0.7576	Intermediate Similarity	NPC469321
0.7568	Intermediate Similarity	NPC22105
0.7568	Intermediate Similarity	NPC134847
0.7568	Intermediate Similarity	NPC304309
0.7568	Intermediate Similarity	NPC288035
0.7568	Intermediate Similarity	NPC113639
0.7568	Intermediate Similarity	NPC285893
0.7568	Intermediate Similarity	NPC136188
0.7568	Intermediate Similarity	NPC28657
0.7568	Intermediate Similarity	NPC162742
0.7568	Intermediate Similarity	NPC230301
0.7538	Intermediate Similarity	NPC52012
0.7536	Intermediate Similarity	NPC469326
0.7536	Intermediate Similarity	NPC205618
0.7536	Intermediate Similarity	NPC261782
0.7534	Intermediate Similarity	NPC476709
0.7532	Intermediate Similarity	NPC324772
0.75	Intermediate Similarity	NPC477522
0.75	Intermediate Similarity	NPC87604
0.75	Intermediate Similarity	NPC9161
0.75	Intermediate Similarity	NPC474216
0.75	Intermediate Similarity	NPC473943
0.75	Intermediate Similarity	NPC473508
0.75	Intermediate Similarity	NPC49422
0.75	Intermediate Similarity	NPC275910
0.7467	Intermediate Similarity	NPC310643
0.7467	Intermediate Similarity	NPC300324
0.7467	Intermediate Similarity	NPC240604
0.7467	Intermediate Similarity	NPC471658
0.7467	Intermediate Similarity	NPC113733
0.7465	Intermediate Similarity	NPC160209
0.7465	Intermediate Similarity	NPC208999
0.7463	Intermediate Similarity	NPC99487
0.7463	Intermediate Similarity	NPC252809
0.746	Intermediate Similarity	NPC192962
0.7436	Intermediate Similarity	NPC320525
0.7436	Intermediate Similarity	NPC470383
0.7432	Intermediate Similarity	NPC471797
0.7429	Intermediate Similarity	NPC469328
0.7429	Intermediate Similarity	NPC267027
0.7429	Intermediate Similarity	NPC162309
0.7424	Intermediate Similarity	NPC181872
0.7424	Intermediate Similarity	NPC155025
0.7403	Intermediate Similarity	NPC84694
0.7403	Intermediate Similarity	NPC81306
0.7403	Intermediate Similarity	NPC472463
0.7403	Intermediate Similarity	NPC109546
0.7403	Intermediate Similarity	NPC28862
0.7403	Intermediate Similarity	NPC328714
0.7403	Intermediate Similarity	NPC47982
0.7403	Intermediate Similarity	NPC143182
0.7397	Intermediate Similarity	NPC242001
0.7397	Intermediate Similarity	NPC41886
0.7397	Intermediate Similarity	NPC471660
0.7391	Intermediate Similarity	NPC287744
0.7391	Intermediate Similarity	NPC140233
0.7391	Intermediate Similarity	NPC300593
0.7368	Intermediate Similarity	NPC471454
0.7368	Intermediate Similarity	NPC214570
0.7368	Intermediate Similarity	NPC34019
0.7361	Intermediate Similarity	NPC329989
0.7361	Intermediate Similarity	NPC239373
0.7353	Intermediate Similarity	NPC225342
0.7353	Intermediate Similarity	NPC63111
0.7353	Intermediate Similarity	NPC475251
0.7342	Intermediate Similarity	NPC248886
0.7342	Intermediate Similarity	NPC101462
0.7333	Intermediate Similarity	NPC257347
0.7333	Intermediate Similarity	NPC60818
0.7333	Intermediate Similarity	NPC141071
0.7333	Intermediate Similarity	NPC23231
0.7333	Intermediate Similarity	NPC471723
0.7324	Intermediate Similarity	NPC114651
0.7324	Intermediate Similarity	NPC73603
0.7308	Intermediate Similarity	NPC209944
0.7308	Intermediate Similarity	NPC164840
0.7308	Intermediate Similarity	NPC26117
0.7308	Intermediate Similarity	NPC234193
0.7308	Intermediate Similarity	NPC241290
0.7297	Intermediate Similarity	NPC14352
0.7297	Intermediate Similarity	NPC471799
0.7297	Intermediate Similarity	NPC234527
0.7286	Intermediate Similarity	NPC61503
0.7286	Intermediate Similarity	NPC308844
0.7286	Intermediate Similarity	NPC471200
0.7273	Intermediate Similarity	NPC307965
0.7273	Intermediate Similarity	NPC318136
0.7273	Intermediate Similarity	NPC477514
0.7273	Intermediate Similarity	NPC76931
0.7273	Intermediate Similarity	NPC6978
0.7273	Intermediate Similarity	NPC18603
0.7273	Intermediate Similarity	NPC138621
0.7273	Intermediate Similarity	NPC312328
0.7273	Intermediate Similarity	NPC167037
0.7273	Intermediate Similarity	NPC285761
0.7273	Intermediate Similarity	NPC244385
0.726	Intermediate Similarity	NPC34834
0.726	Intermediate Similarity	NPC145498
0.7258	Intermediate Similarity	NPC329773
0.725	Intermediate Similarity	NPC470384
0.725	Intermediate Similarity	NPC320548
0.7246	Intermediate Similarity	NPC474480
0.7237	Intermediate Similarity	NPC202642
0.7237	Intermediate Similarity	NPC237460
0.7237	Intermediate Similarity	NPC126969
0.7237	Intermediate Similarity	NPC470362
0.7237	Intermediate Similarity	NPC46160
0.7237	Intermediate Similarity	NPC96319
0.7237	Intermediate Similarity	NPC244488
0.7237	Intermediate Similarity	NPC247325
0.7237	Intermediate Similarity	NPC134330
0.7237	Intermediate Similarity	NPC189883
0.7237	Intermediate Similarity	NPC129165
0.7237	Intermediate Similarity	NPC73875
0.7231	Intermediate Similarity	NPC281590
0.7222	Intermediate Similarity	NPC470040
0.7222	Intermediate Similarity	NPC305698
0.7215	Intermediate Similarity	NPC264245
0.7215	Intermediate Similarity	NPC474731
0.7215	Intermediate Similarity	NPC474759
0.7215	Intermediate Similarity	NPC7505
0.7215	Intermediate Similarity	NPC474683
0.7215	Intermediate Similarity	NPC474752
0.7215	Intermediate Similarity	NPC23852
0.7215	Intermediate Similarity	NPC209620
0.7215	Intermediate Similarity	NPC471661
0.7215	Intermediate Similarity	NPC82986
0.7215	Intermediate Similarity	NPC474531
0.7215	Intermediate Similarity	NPC47761
0.7215	Intermediate Similarity	NPC136150
0.7206	Intermediate Similarity	NPC66020
0.72	Intermediate Similarity	NPC477138
0.72	Intermediate Similarity	NPC471525
0.72	Intermediate Similarity	NPC102463
0.72	Intermediate Similarity	NPC243342
0.72	Intermediate Similarity	NPC91858
0.7188	Intermediate Similarity	NPC474496
0.7183	Intermediate Similarity	NPC311736
0.7183	Intermediate Similarity	NPC202017
0.7183	Intermediate Similarity	NPC326310
0.7179	Intermediate Similarity	NPC30986
0.7179	Intermediate Similarity	NPC80530
0.7179	Intermediate Similarity	NPC476701
0.7179	Intermediate Similarity	NPC1319
0.7179	Intermediate Similarity	NPC209430
0.7179	Intermediate Similarity	NPC273410
0.7162	Intermediate Similarity	NPC167706
0.7162	Intermediate Similarity	NPC477792
0.716	Intermediate Similarity	NPC205845
0.716	Intermediate Similarity	NPC185568
0.716	Intermediate Similarity	NPC474493

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 NPC272125 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	2558
0.2-0.3	4144
0.3-0.4	1689
0.4-0.5	437
0.5-0.6	124
0.6-0.7	43
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
0.7917	Intermediate Similarity	NPD6924	Approved
0.7917	Intermediate Similarity	NPD6926	Approved
0.7703	Intermediate Similarity	NPD6933	Approved
0.7632	Intermediate Similarity	NPD6929	Approved
0.7606	Intermediate Similarity	NPD6922	Approved
0.7606	Intermediate Similarity	NPD6923	Approved
0.7568	Intermediate Similarity	NPD7339	Approved
0.7568	Intermediate Similarity	NPD6942	Approved
0.7532	Intermediate Similarity	NPD6930	Phase 2
0.7532	Intermediate Similarity	NPD6931	Approved
0.7532	Intermediate Similarity	NPD7509	Discontinued
0.75	Intermediate Similarity	NPD7144	Approved
0.75	Intermediate Similarity	NPD7143	Approved
0.7397	Intermediate Similarity	NPD7150	Approved
0.7397	Intermediate Similarity	NPD7151	Approved
0.7397	Intermediate Similarity	NPD7152	Approved
0.7368	Intermediate Similarity	NPD5776	Phase 2
0.7368	Intermediate Similarity	NPD6932	Approved
0.7368	Intermediate Similarity	NPD6925	Approved
0.7308	Intermediate Similarity	NPD7332	Phase 2
0.7273	Intermediate Similarity	NPD7145	Approved
0.7273	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6695	Phase 3
0.7237	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6898	Phase 1
0.7179	Intermediate Similarity	NPD6683	Phase 2
0.716	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7514	Phase 3
0.7089	Intermediate Similarity	NPD7525	Registered
0.7073	Intermediate Similarity	NPD6893	Approved
0.7037	Intermediate Similarity	NPD5362	Discontinued
0.7	Intermediate Similarity	NPD6902	Approved
0.6951	Remote Similarity	NPD4786	Approved
0.6905	Remote Similarity	NPD7750	Discontinued
0.6905	Remote Similarity	NPD7524	Approved
0.6875	Remote Similarity	NPD4819	Approved
0.6875	Remote Similarity	NPD4821	Approved
0.6875	Remote Similarity	NPD4820	Approved
0.6875	Remote Similarity	NPD4822	Approved
0.6857	Remote Similarity	NPD368	Approved
0.6835	Remote Similarity	NPD4271	Approved
0.6835	Remote Similarity	NPD4268	Approved
0.6829	Remote Similarity	NPD5332	Approved
0.6829	Remote Similarity	NPD7154	Phase 3
0.6829	Remote Similarity	NPD5331	Approved
0.679	Remote Similarity	NPD4790	Discontinued
0.6753	Remote Similarity	NPD4784	Approved
0.6753	Remote Similarity	NPD4785	Approved
0.675	Remote Similarity	NPD7645	Phase 2
0.6716	Remote Similarity	NPD342	Phase 1
0.6711	Remote Similarity	NPD4243	Approved
0.6707	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7087	Discontinued
0.6585	Remote Similarity	NPD5369	Approved
0.6512	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD6435	Approved
0.6506	Remote Similarity	NPD4269	Approved
0.6506	Remote Similarity	NPD4270	Approved
0.6477	Remote Similarity	NPD7136	Phase 2
0.6471	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4748	Discontinued
0.6395	Remote Similarity	NPD5279	Phase 3
0.6364	Remote Similarity	NPD5328	Approved
0.6353	Remote Similarity	NPD3666	Approved
0.6353	Remote Similarity	NPD3133	Approved
0.6353	Remote Similarity	NPD3665	Phase 1
0.6279	Remote Similarity	NPD5363	Approved
0.6265	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD4190	Phase 3
0.625	Remote Similarity	NPD5275	Approved
0.6222	Remote Similarity	NPD6079	Approved
0.6222	Remote Similarity	NPD7637	Suspended
0.6207	Remote Similarity	NPD3618	Phase 1
0.6207	Remote Similarity	NPD5786	Approved
0.6196	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4753	Phase 2
0.618	Remote Similarity	NPD1695	Approved
0.618	Remote Similarity	NPD6101	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6145	Remote Similarity	NPD4195	Approved
0.6136	Remote Similarity	NPD4250	Approved
0.6136	Remote Similarity	NPD4251	Approved
0.6094	Remote Similarity	NPD4265	Approved
0.6053	Remote Similarity	NPD7331	Phase 2
0.6044	Remote Similarity	NPD6411	Approved
0.6023	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD4732	Discontinued
0.5978	Remote Similarity	NPD4202	Approved
0.5978	Remote Similarity	NPD5779	Approved
0.5978	Remote Similarity	NPD5778	Approved
0.5977	Remote Similarity	NPD3668	Phase 3
0.5976	Remote Similarity	NPD1346	Approved
0.5934	Remote Similarity	NPD7838	Discovery
0.5934	Remote Similarity	NPD5785	Approved
0.593	Remote Similarity	NPD4223	Phase 3
0.593	Remote Similarity	NPD4221	Approved
0.5921	Remote Similarity	NPD7341	Phase 2
0.5914	Remote Similarity	NPD5282	Discontinued
0.5909	Remote Similarity	NPD5329	Approved
0.5909	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.59	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6083	Phase 2
0.5895	Remote Similarity	NPD6084	Phase 2
0.5895	Remote Similarity	NPD4755	Approved
0.5882	Remote Similarity	NPD6371	Approved
0.5862	Remote Similarity	NPD4788	Approved
0.5851	Remote Similarity	NPD5210	Approved
0.5851	Remote Similarity	NPD4629	Approved
0.5823	Remote Similarity	NPD1082	Approved
0.58	Remote Similarity	NPD6640	Phase 3
0.5795	Remote Similarity	NPD4197	Approved
0.5795	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5222	Approved
0.5789	Remote Similarity	NPD3197	Phase 1
0.5789	Remote Similarity	NPD4697	Phase 3
0.5789	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5221	Approved
0.5773	Remote Similarity	NPD5285	Approved
0.5773	Remote Similarity	NPD4700	Approved
0.5773	Remote Similarity	NPD5286	Approved
0.5773	Remote Similarity	NPD4696	Approved
0.5761	Remote Similarity	NPD46	Approved
0.5761	Remote Similarity	NPD6698	Approved
0.5758	Remote Similarity	NPD384	Approved
0.5758	Remote Similarity	NPD385	Approved
0.5729	Remote Similarity	NPD5173	Approved
0.5714	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4518	Approved
0.5699	Remote Similarity	NPD7983	Approved
0.5699	Remote Similarity	NPD7515	Phase 2
0.5698	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD4695	Discontinued
0.5694	Remote Similarity	NPD4219	Approved
0.5684	Remote Similarity	NPD5695	Phase 3
0.5676	Remote Similarity	NPD3198	Approved
0.567	Remote Similarity	NPD4225	Approved
0.567	Remote Similarity	NPD7638	Approved
0.5667	Remote Similarity	NPD4694	Approved
0.5667	Remote Similarity	NPD4689	Approved
0.5667	Remote Similarity	NPD4693	Phase 3
0.5667	Remote Similarity	NPD7146	Approved
0.5667	Remote Similarity	NPD5205	Approved
0.5667	Remote Similarity	NPD4690	Approved
0.5667	Remote Similarity	NPD5280	Approved
0.5667	Remote Similarity	NPD4138	Approved
0.5667	Remote Similarity	NPD7521	Approved
0.5667	Remote Similarity	NPD6684	Approved
0.5667	Remote Similarity	NPD7334	Approved
0.5667	Remote Similarity	NPD4688	Approved
0.5667	Remote Similarity	NPD5690	Phase 2
0.5667	Remote Similarity	NPD6409	Approved
0.5667	Remote Similarity	NPD5330	Approved
0.5657	Remote Similarity	NPD4633	Approved
0.5657	Remote Similarity	NPD5224	Approved
0.5657	Remote Similarity	NPD5225	Approved
0.5657	Remote Similarity	NPD5211	Phase 2
0.5657	Remote Similarity	NPD5226	Approved
0.5652	Remote Similarity	NPD6051	Approved
0.5644	Remote Similarity	NPD7128	Approved
0.5644	Remote Similarity	NPD6675	Approved
0.5644	Remote Similarity	NPD5739	Approved
0.5644	Remote Similarity	NPD6402	Approved
0.5632	Remote Similarity	NPD857	Phase 3
0.5625	Remote Similarity	NPD15	Approved
0.5625	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD791	Approved
0.5619	Remote Similarity	NPD6053	Discontinued
0.5612	Remote Similarity	NPD7640	Approved
0.5612	Remote Similarity	NPD7639	Approved
0.56	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5175	Approved
0.56	Remote Similarity	NPD5174	Approved
0.56	Remote Similarity	NPD1145	Discontinued

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