NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	326.404
LogP:	4.579
LogD:	3.83
LogS:	-4.124
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	5.585
Fsp3:	0.9
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:	-4.838
MDCK Permeability:	9.316035175288562e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.903
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.385
Plasma Protein Binding (PPB):	67.11249542236328%
Volume Distribution (VD):	0.769
Pgp-substrate:	15.11409854888916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.278
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.419
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	13.301
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.554
Drug-inuced Liver Injury (DILI):	0.13
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.176
Maximum Recommended Daily Dose:	0.848
Skin Sensitization:	0.425
Carcinogencity:	0.505
Eye Corrosion:	0.059
Eye Irritation:	0.109
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC476737

Natural Product ID:	NPC476737
*Common Name:**	TUJQVRFWMWRMIO-GNVSMLMZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TUJQVRFWMWRMIO-GNVSMLMZSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-14-11-20-10-7-16-18(2,13-21)8-4-9-19(16,3)17(20)6-5-15(14)12-20/h15-17,21H,1,4-13H2,2-3H3/t15-,16+,17-,18-,19+,20+/m0/s1
SMILES:	OC[C@]1(C)CCC[C@@]2([C@@H]1CC[C@@]13[C@H]2CC[C@@H](C3)C(=C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512447
PubChem CID:	24883422
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO33342	Bruguiera gymnorrhiza	Species	Rhizophoraceae	Eukaryota	stems	Xiamen, China	2002-JUN	PMID[15387677]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO33342	Bruguiera gymnorrhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562850]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
GI50	2
IC50	4
Others	9

Activity Type	# Activity
Cell Line	3
Individual Protein	6
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	GI50	=	18.2	ug.mL-1	PMID[464818]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	6.8	ug.mL-1	PMID[464818]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	32.8	ug.mL-1	PMID[464818]
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	=	28.58	%	PMID[464820]
NPT4862	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	Inhibition	=	20.43	%	PMID[464820]
NPT4861	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Mus musculus	IC50	>	1000000.0	nM	PMID[464820]
NPT1138	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Homo sapiens	IC50	=	10000.0	nM	PMID[464820]
NPT4862	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	IC50	=	1553.0	nM	PMID[464820]
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	IC50	=	1417.0	nM	PMID[464820]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	66.0	%	PMID[464816]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	72.0	%	PMID[464816]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	100.0	%	PMID[464816]
NPT2	Others	Unspecified		Inhibition	=	7.0	%	PMID[464819]
NPT2	Others	Unspecified		Ratio IC50	>	640.0	n.a.	PMID[464820]
NPT2	Others	Unspecified		Ratio IC50	=	7.0	n.a.	PMID[464820]

☑ 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 NPC476737 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	148
0.1-0.2	2321
0.2-0.3	15570
0.3-0.4	10786
0.4-0.5	5497
0.5-0.6	5212
0.6-0.7	2358
0.7-0.8	661
0.8-0.85	104
0.85-0.9	32
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC27243
0.9231	High Similarity	NPC45296
0.9091	High Similarity	NPC111234
0.9091	High Similarity	NPC164045
0.8955	High Similarity	NPC472506
0.8955	High Similarity	NPC195489
0.8923	High Similarity	NPC160209
0.8824	High Similarity	NPC62657
0.8824	High Similarity	NPC476736
0.8824	High Similarity	NPC254509
0.8824	High Similarity	NPC5046
0.8824	High Similarity	NPC49168
0.8824	High Similarity	NPC308440
0.8824	High Similarity	NPC192638
0.8824	High Similarity	NPC25511
0.8824	High Similarity	NPC145552
0.8824	High Similarity	NPC472503
0.8824	High Similarity	NPC196358
0.8696	High Similarity	NPC230704
0.8696	High Similarity	NPC212879
0.8696	High Similarity	NPC200243
0.8696	High Similarity	NPC240235
0.8696	High Similarity	NPC231256
0.8696	High Similarity	NPC3403
0.8696	High Similarity	NPC104387
0.8696	High Similarity	NPC178383
0.8696	High Similarity	NPC185536
0.8696	High Similarity	NPC70982
0.8571	High Similarity	NPC91573
0.8571	High Similarity	NPC86305
0.8571	High Similarity	NPC93662
0.8571	High Similarity	NPC237460
0.8571	High Similarity	NPC147524
0.8571	High Similarity	NPC38141
0.8571	High Similarity	NPC14112
0.8571	High Similarity	NPC78067
0.8571	High Similarity	NPC278091
0.8485	Intermediate Similarity	NPC197805
0.8451	Intermediate Similarity	NPC257191
0.8451	Intermediate Similarity	NPC307336
0.8451	Intermediate Similarity	NPC202540
0.8451	Intermediate Similarity	NPC331618
0.8451	Intermediate Similarity	NPC138502
0.8451	Intermediate Similarity	NPC119355
0.8451	Intermediate Similarity	NPC212241
0.8451	Intermediate Similarity	NPC260301
0.8451	Intermediate Similarity	NPC248830
0.8429	Intermediate Similarity	NPC162742
0.8429	Intermediate Similarity	NPC288035
0.8429	Intermediate Similarity	NPC136188
0.8429	Intermediate Similarity	NPC230301
0.8429	Intermediate Similarity	NPC257347
0.8429	Intermediate Similarity	NPC285893
0.8429	Intermediate Similarity	NPC304309
0.8429	Intermediate Similarity	NPC141071
0.8429	Intermediate Similarity	NPC471723
0.8429	Intermediate Similarity	NPC28657
0.8429	Intermediate Similarity	NPC103822
0.8429	Intermediate Similarity	NPC134847
0.8429	Intermediate Similarity	NPC22105
0.8406	Intermediate Similarity	NPC474743
0.8387	Intermediate Similarity	NPC476735
0.8333	Intermediate Similarity	NPC65897
0.8333	Intermediate Similarity	NPC138621
0.8333	Intermediate Similarity	NPC85346
0.8333	Intermediate Similarity	NPC285761
0.8333	Intermediate Similarity	NPC301707
0.8333	Intermediate Similarity	NPC476039
0.8333	Intermediate Similarity	NPC222366
0.8333	Intermediate Similarity	NPC102708
0.8333	Intermediate Similarity	NPC42853
0.8333	Intermediate Similarity	NPC477817
0.8333	Intermediate Similarity	NPC6978
0.8333	Intermediate Similarity	NPC472502
0.8333	Intermediate Similarity	NPC472501
0.8333	Intermediate Similarity	NPC475
0.8333	Intermediate Similarity	NPC244385
0.8333	Intermediate Similarity	NPC472500
0.8333	Intermediate Similarity	NPC472342
0.8333	Intermediate Similarity	NPC472499
0.8333	Intermediate Similarity	NPC477819
0.8333	Intermediate Similarity	NPC286669
0.8333	Intermediate Similarity	NPC302041
0.8333	Intermediate Similarity	NPC31828
0.8333	Intermediate Similarity	NPC167037
0.831	Intermediate Similarity	NPC189883
0.831	Intermediate Similarity	NPC300324
0.831	Intermediate Similarity	NPC107059
0.831	Intermediate Similarity	NPC247325
0.831	Intermediate Similarity	NPC134330
0.831	Intermediate Similarity	NPC129165
0.831	Intermediate Similarity	NPC321381
0.831	Intermediate Similarity	NPC113733
0.831	Intermediate Similarity	NPC321016
0.831	Intermediate Similarity	NPC240604
0.831	Intermediate Similarity	NPC244488
0.8261	Intermediate Similarity	NPC301226
0.8219	Intermediate Similarity	NPC24504
0.8219	Intermediate Similarity	NPC80530
0.8219	Intermediate Similarity	NPC476316
0.8219	Intermediate Similarity	NPC116119
0.8219	Intermediate Similarity	NPC472742
0.8219	Intermediate Similarity	NPC273410
0.8219	Intermediate Similarity	NPC49627
0.8219	Intermediate Similarity	NPC201459
0.8219	Intermediate Similarity	NPC475727
0.8219	Intermediate Similarity	NPC5604
0.8219	Intermediate Similarity	NPC49599
0.8219	Intermediate Similarity	NPC80297
0.8194	Intermediate Similarity	NPC155986
0.8194	Intermediate Similarity	NPC318495
0.8194	Intermediate Similarity	NPC106078
0.8194	Intermediate Similarity	NPC34019
0.8194	Intermediate Similarity	NPC198968
0.8169	Intermediate Similarity	NPC121744
0.8169	Intermediate Similarity	NPC322353
0.8169	Intermediate Similarity	NPC471468
0.8169	Intermediate Similarity	NPC118508
0.8143	Intermediate Similarity	NPC474140
0.8143	Intermediate Similarity	NPC211009
0.8116	Intermediate Similarity	NPC475728
0.8108	Intermediate Similarity	NPC13554
0.8108	Intermediate Similarity	NPC236237
0.8108	Intermediate Similarity	NPC102253
0.8108	Intermediate Similarity	NPC475679
0.8108	Intermediate Similarity	NPC78545
0.8108	Intermediate Similarity	NPC322313
0.8108	Intermediate Similarity	NPC71535
0.8108	Intermediate Similarity	NPC47149
0.8088	Intermediate Similarity	NPC2648
0.8088	Intermediate Similarity	NPC216460
0.8088	Intermediate Similarity	NPC32055
0.8082	Intermediate Similarity	NPC307965
0.8082	Intermediate Similarity	NPC477522
0.8082	Intermediate Similarity	NPC473943
0.8082	Intermediate Similarity	NPC477514
0.8082	Intermediate Similarity	NPC76931
0.8082	Intermediate Similarity	NPC87604
0.8082	Intermediate Similarity	NPC474216
0.8082	Intermediate Similarity	NPC18603
0.8082	Intermediate Similarity	NPC312328
0.8065	Intermediate Similarity	NPC264779
0.806	Intermediate Similarity	NPC476406
0.806	Intermediate Similarity	NPC149680
0.8056	Intermediate Similarity	NPC202642
0.8056	Intermediate Similarity	NPC73875
0.8056	Intermediate Similarity	NPC470362
0.8056	Intermediate Similarity	NPC46160
0.803	Intermediate Similarity	NPC101128
0.803	Intermediate Similarity	NPC68656
0.8028	Intermediate Similarity	NPC100334
0.8028	Intermediate Similarity	NPC469593
0.8028	Intermediate Similarity	NPC469534
0.8028	Intermediate Similarity	NPC469533
0.8	Intermediate Similarity	NPC148174
0.8	Intermediate Similarity	NPC71460
0.8	Intermediate Similarity	NPC157655
0.8	Intermediate Similarity	NPC218585
0.8	Intermediate Similarity	NPC103754
0.8	Intermediate Similarity	NPC474484
0.7973	Intermediate Similarity	NPC109546
0.7973	Intermediate Similarity	NPC84694
0.7973	Intermediate Similarity	NPC328714
0.7973	Intermediate Similarity	NPC143182
0.7973	Intermediate Similarity	NPC30986
0.7973	Intermediate Similarity	NPC28862
0.7973	Intermediate Similarity	NPC47982
0.7973	Intermediate Similarity	NPC81306
0.7973	Intermediate Similarity	NPC1319
0.7973	Intermediate Similarity	NPC209430
0.7971	Intermediate Similarity	NPC210323
0.7945	Intermediate Similarity	NPC214570
0.7941	Intermediate Similarity	NPC308522
0.7941	Intermediate Similarity	NPC68703
0.7941	Intermediate Similarity	NPC69649
0.7941	Intermediate Similarity	NPC74885
0.7917	Intermediate Similarity	NPC144075
0.791	Intermediate Similarity	NPC208198
0.791	Intermediate Similarity	NPC2728
0.791	Intermediate Similarity	NPC258595
0.791	Intermediate Similarity	NPC60837
0.791	Intermediate Similarity	NPC163678
0.791	Intermediate Similarity	NPC11555
0.791	Intermediate Similarity	NPC282619
0.791	Intermediate Similarity	NPC172613
0.7895	Intermediate Similarity	NPC477858
0.7895	Intermediate Similarity	NPC145143
0.7895	Intermediate Similarity	NPC296701
0.7895	Intermediate Similarity	NPC477599
0.7895	Intermediate Similarity	NPC218616
0.7895	Intermediate Similarity	NPC472504
0.7887	Intermediate Similarity	NPC244708
0.7887	Intermediate Similarity	NPC471799
0.7887	Intermediate Similarity	NPC330659
0.7887	Intermediate Similarity	NPC182717
0.7887	Intermediate Similarity	NPC161187
0.7887	Intermediate Similarity	NPC201373
0.7879	Intermediate Similarity	NPC114891
0.7867	Intermediate Similarity	NPC164840
0.7867	Intermediate Similarity	NPC236112

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 NPC476737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	2648
0.2-0.3	4471
0.3-0.4	1289
0.4-0.5	252
0.5-0.6	191
0.6-0.7	108
0.7-0.8	40
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8429	Intermediate Similarity	NPD6942	Approved
0.8429	Intermediate Similarity	NPD7339	Approved
0.8108	Intermediate Similarity	NPD7525	Registered
0.8	Intermediate Similarity	NPD4243	Approved
0.7808	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4788	Approved
0.7778	Intermediate Similarity	NPD4785	Approved
0.7778	Intermediate Similarity	NPD6924	Approved
0.7778	Intermediate Similarity	NPD6926	Approved
0.7778	Intermediate Similarity	NPD4784	Approved
0.7714	Intermediate Similarity	NPD6923	Approved
0.7714	Intermediate Similarity	NPD6922	Approved
0.7606	Intermediate Similarity	NPD7144	Approved
0.7606	Intermediate Similarity	NPD7143	Approved
0.7595	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6933	Approved
0.75	Intermediate Similarity	NPD7645	Phase 2
0.75	Intermediate Similarity	NPD7150	Approved
0.75	Intermediate Similarity	NPD7152	Approved
0.75	Intermediate Similarity	NPD7151	Approved
0.7468	Intermediate Similarity	NPD4786	Approved
0.7432	Intermediate Similarity	NPD4190	Phase 3
0.7432	Intermediate Similarity	NPD5275	Approved
0.7273	Intermediate Similarity	NPD6929	Approved
0.7222	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3667	Approved
0.7179	Intermediate Similarity	NPD6930	Phase 2
0.7179	Intermediate Similarity	NPD6931	Approved
0.7123	Intermediate Similarity	NPD4787	Phase 1
0.7123	Intermediate Similarity	NPD4789	Approved
0.7051	Intermediate Similarity	NPD4195	Approved
0.7037	Intermediate Similarity	NPD3666	Approved
0.7037	Intermediate Similarity	NPD3665	Phase 1
0.7037	Intermediate Similarity	NPD3133	Approved
0.7027	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5328	Approved
0.7013	Intermediate Similarity	NPD5776	Phase 2
0.7013	Intermediate Similarity	NPD6932	Approved
0.7013	Intermediate Similarity	NPD6925	Approved
0.6988	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4748	Discontinued
0.6962	Remote Similarity	NPD7509	Discontinued
0.6923	Remote Similarity	NPD7145	Approved
0.6914	Remote Similarity	NPD6695	Phase 3
0.6901	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4244	Approved
0.6892	Remote Similarity	NPD4245	Approved
0.6867	Remote Similarity	NPD3618	Phase 1
0.686	Remote Similarity	NPD8034	Phase 2
0.686	Remote Similarity	NPD6079	Approved
0.686	Remote Similarity	NPD8035	Phase 2
0.6849	Remote Similarity	NPD6705	Phase 1
0.6842	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6683	Phase 2
0.6829	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4753	Phase 2
0.679	Remote Similarity	NPD4223	Phase 3
0.679	Remote Similarity	NPD4221	Approved
0.6757	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3698	Phase 2
0.675	Remote Similarity	NPD7514	Phase 3
0.6747	Remote Similarity	NPD6893	Approved
0.6747	Remote Similarity	NPD5329	Approved
0.6709	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6902	Approved
0.6627	Remote Similarity	NPD4197	Approved
0.6622	Remote Similarity	NPD5360	Phase 3
0.6622	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6399	Phase 3
0.6591	Remote Similarity	NPD4202	Approved
0.6588	Remote Similarity	NPD7524	Approved
0.6588	Remote Similarity	NPD7750	Discontinued
0.6582	Remote Similarity	NPD6116	Phase 1
0.6575	Remote Similarity	NPD4224	Phase 2
0.6543	Remote Similarity	NPD7332	Phase 2
0.65	Remote Similarity	NPD6114	Approved
0.65	Remote Similarity	NPD6115	Approved
0.65	Remote Similarity	NPD6118	Approved
0.65	Remote Similarity	NPD3617	Approved
0.65	Remote Similarity	NPD6697	Approved
0.6484	Remote Similarity	NPD6084	Phase 2
0.6484	Remote Similarity	NPD6083	Phase 2
0.6477	Remote Similarity	NPD7515	Phase 2
0.6471	Remote Similarity	NPD5205	Approved
0.6471	Remote Similarity	NPD4138	Approved
0.6471	Remote Similarity	NPD4690	Approved
0.6471	Remote Similarity	NPD4688	Approved
0.6471	Remote Similarity	NPD4693	Phase 3
0.6471	Remote Similarity	NPD4689	Approved
0.6463	Remote Similarity	NPD6898	Phase 1
0.6444	Remote Similarity	NPD4629	Approved
0.6444	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD3668	Phase 3
0.6413	Remote Similarity	NPD7638	Approved
0.6374	Remote Similarity	NPD5222	Approved
0.6374	Remote Similarity	NPD5221	Approved
0.6374	Remote Similarity	NPD4697	Phase 3
0.6374	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6081	Approved
0.6344	Remote Similarity	NPD7639	Approved
0.6344	Remote Similarity	NPD7640	Approved
0.6341	Remote Similarity	NPD6928	Phase 2
0.6329	Remote Similarity	NPD3703	Phase 2
0.6329	Remote Similarity	NPD8264	Approved
0.6324	Remote Similarity	NPD342	Phase 1
0.6322	Remote Similarity	NPD4723	Approved
0.6322	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6672	Approved
0.6322	Remote Similarity	NPD5737	Approved
0.6322	Remote Similarity	NPD4722	Approved
0.6304	Remote Similarity	NPD5173	Approved
0.6304	Remote Similarity	NPD4755	Approved
0.6292	Remote Similarity	NPD7087	Discontinued
0.6279	Remote Similarity	NPD6409	Approved
0.6279	Remote Similarity	NPD7146	Approved
0.6279	Remote Similarity	NPD5280	Approved
0.6279	Remote Similarity	NPD5330	Approved
0.6279	Remote Similarity	NPD7521	Approved
0.6279	Remote Similarity	NPD6684	Approved
0.6279	Remote Similarity	NPD4694	Approved
0.6279	Remote Similarity	NPD7334	Approved
0.6279	Remote Similarity	NPD5690	Phase 2
0.6265	Remote Similarity	NPD4692	Approved
0.6265	Remote Similarity	NPD4139	Approved
0.625	Remote Similarity	NPD6051	Approved
0.617	Remote Similarity	NPD4700	Approved
0.617	Remote Similarity	NPD5286	Approved
0.617	Remote Similarity	NPD5285	Approved
0.617	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD7748	Approved
0.6154	Remote Similarity	NPD4758	Discontinued
0.6145	Remote Similarity	NPD4695	Discontinued
0.6136	Remote Similarity	NPD6903	Approved
0.6125	Remote Similarity	NPD3702	Approved
0.6105	Remote Similarity	NPD5223	Approved
0.6098	Remote Similarity	NPD3671	Phase 1
0.6094	Remote Similarity	NPD384	Approved
0.6094	Remote Similarity	NPD385	Approved
0.6092	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4623	Approved
0.6092	Remote Similarity	NPD6098	Approved
0.6092	Remote Similarity	NPD4519	Discontinued
0.6087	Remote Similarity	NPD5695	Phase 3
0.6064	Remote Similarity	NPD5696	Approved
0.6064	Remote Similarity	NPD5290	Discontinued
0.6042	Remote Similarity	NPD5211	Phase 2
0.6042	Remote Similarity	NPD5226	Approved
0.6042	Remote Similarity	NPD5224	Approved
0.6042	Remote Similarity	NPD5225	Approved
0.6042	Remote Similarity	NPD4633	Approved
0.6026	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD4747	Approved
0.6026	Remote Similarity	NPD6939	Phase 2
0.602	Remote Similarity	NPD7128	Approved
0.602	Remote Similarity	NPD6675	Approved
0.602	Remote Similarity	NPD5739	Approved
0.602	Remote Similarity	NPD6402	Approved
0.5979	Remote Similarity	NPD5175	Approved
0.5979	Remote Similarity	NPD4754	Approved
0.5979	Remote Similarity	NPD5174	Approved
0.5974	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7902	Approved
0.5949	Remote Similarity	NPD5777	Approved
0.5934	Remote Similarity	NPD7637	Suspended
0.5934	Remote Similarity	NPD5281	Approved
0.5934	Remote Similarity	NPD5284	Approved
0.5918	Remote Similarity	NPD5141	Approved
0.5904	Remote Similarity	NPD5364	Discontinued
0.59	Remote Similarity	NPD6899	Approved
0.59	Remote Similarity	NPD7320	Approved
0.59	Remote Similarity	NPD6881	Approved
0.5897	Remote Similarity	NPD4137	Phase 3
0.589	Remote Similarity	NPD1145	Discontinued
0.5889	Remote Similarity	NPD6673	Approved
0.5889	Remote Similarity	NPD6904	Approved
0.5889	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6080	Approved
0.5876	Remote Similarity	NPD7632	Discontinued
0.5859	Remote Similarity	NPD4767	Approved
0.5859	Remote Similarity	NPD4768	Approved
0.5854	Remote Similarity	NPD1346	Approved
0.5842	Remote Similarity	NPD6372	Approved
0.5842	Remote Similarity	NPD6373	Approved
0.5824	Remote Similarity	NPD4096	Approved
0.5824	Remote Similarity	NPD7136	Phase 2
0.5823	Remote Similarity	NPD4691	Approved
0.5814	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD368	Approved
0.5806	Remote Similarity	NPD5771	Approved
0.5802	Remote Similarity	NPD5733	Approved
0.58	Remote Similarity	NPD5697	Approved
0.58	Remote Similarity	NPD5701	Approved
0.58	Remote Similarity	NPD6412	Phase 2
0.5784	Remote Similarity	NPD6883	Approved
0.5784	Remote Similarity	NPD7290	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