NPASS Compound

Structure

NPC91594 OpenBabel07101719152D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -1.5000 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 -0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 3.4641 0.0000 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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.6340 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 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 2 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 5.8301 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 18 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 1 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 18 1 6 0 0 0 17 22 1 0 0 0 0 18 2 1 1 0 0 0 19 3 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	3.436
LogD:	3.593
LogS:	-4.173
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	4.71
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.67
MDCK Permeability:	2.5720322810229845e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.444
Plasma Protein Binding (PPB):	93.75409698486328%
Volume Distribution (VD):	1.149
Pgp-substrate:	4.19723653793335%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.251
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.341
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	6.36
Half-life (T1/2):	0.447

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.566
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.564
Carcinogencity:	0.1
Eye Corrosion:	0.642
Eye Irritation:	0.91
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC91594

Natural Product ID:	NPC91594
*Common Name:**	OGDKBMIXPVDZEL-CFSBILQPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OGDKBMIXPVDZEL-CFSBILQPSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-5-18(2)12-9-15-14(17(18)22)7-8-16-19(3,13-21)10-6-11-20(15,16)4/h5,7,15-17,21-22H,1,6,8-13H2,2-4H3/t15-,16-,17+,18-,19-,20+/m0/s1
SMILES:	OC[C@]1(C)CCC[C@]2([C@H]1CC=C1[C@@H]2CC[C@]([C@@H]1O)(C)C=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3590336
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
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26110519]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	EC50	=	7600.0	nM	PMID[558206]

☑ 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 NPC91594 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	178
0.1-0.2	1297
0.2-0.3	5213
0.3-0.4	14784
0.4-0.5	9992
0.5-0.6	6245
0.6-0.7	3456
0.7-0.8	1198
0.8-0.85	218
0.85-0.9	84
0.9-0.95	31
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9467	High Similarity	NPC476646
0.9333	High Similarity	NPC96362
0.9324	High Similarity	NPC83351
0.9324	High Similarity	NPC167891
0.9315	High Similarity	NPC265588
0.9306	High Similarity	NPC243342
0.9306	High Similarity	NPC477138
0.9296	High Similarity	NPC242001
0.9189	High Similarity	NPC471798
0.9189	High Similarity	NPC470758
0.9189	High Similarity	NPC470711
0.9178	High Similarity	NPC291503
0.9167	High Similarity	NPC182717
0.9167	High Similarity	NPC471799
0.9155	High Similarity	NPC34834
0.9155	High Similarity	NPC145498
0.9091	High Similarity	NPC49964
0.9079	High Similarity	NPC295131
0.9079	High Similarity	NPC234193
0.9067	High Similarity	NPC476314
0.9067	High Similarity	NPC11908
0.9054	High Similarity	NPC470749
0.9054	High Similarity	NPC253190
0.9041	High Similarity	NPC471797
0.9041	High Similarity	NPC476366
0.9041	High Similarity	NPC91858
0.9041	High Similarity	NPC201048
0.8961	High Similarity	NPC264245
0.8961	High Similarity	NPC249423
0.8947	High Similarity	NPC81306
0.8947	High Similarity	NPC28862
0.8947	High Similarity	NPC143182
0.8947	High Similarity	NPC47982
0.8947	High Similarity	NPC30986
0.8947	High Similarity	NPC209430
0.8947	High Similarity	NPC84694
0.8947	High Similarity	NPC109546
0.8919	High Similarity	NPC66566
0.8919	High Similarity	NPC477923
0.8919	High Similarity	NPC32832
0.8875	High Similarity	NPC261266
0.8861	High Similarity	NPC205845
0.8846	High Similarity	NPC87489
0.8846	High Similarity	NPC296701
0.8846	High Similarity	NPC50964
0.8846	High Similarity	NPC101462
0.8846	High Similarity	NPC218616
0.8831	High Similarity	NPC209944
0.8831	High Similarity	NPC241290
0.8831	High Similarity	NPC164840
0.8816	High Similarity	NPC22955
0.8816	High Similarity	NPC470396
0.8816	High Similarity	NPC474216
0.8816	High Similarity	NPC474989
0.8816	High Similarity	NPC99168
0.88	High Similarity	NPC106432
0.88	High Similarity	NPC244488
0.88	High Similarity	NPC247325
0.8784	High Similarity	NPC306727
0.8784	High Similarity	NPC100334
0.8767	High Similarity	NPC110799
0.8767	High Similarity	NPC167706
0.875	High Similarity	NPC274448
0.875	High Similarity	NPC471560
0.8734	High Similarity	NPC317458
0.8734	High Similarity	NPC470384
0.8732	High Similarity	NPC114651
0.8732	High Similarity	NPC197805
0.8732	High Similarity	NPC68703
0.8732	High Similarity	NPC69649
0.8718	High Similarity	NPC47761
0.8718	High Similarity	NPC23852
0.8718	High Similarity	NPC209620
0.8701	High Similarity	NPC53744
0.8701	High Similarity	NPC291379
0.8684	High Similarity	NPC90979
0.8684	High Similarity	NPC40394
0.8684	High Similarity	NPC477924
0.8684	High Similarity	NPC157996
0.8684	High Similarity	NPC101475
0.8684	High Similarity	NPC472805
0.8684	High Similarity	NPC34177
0.8684	High Similarity	NPC130136
0.8649	High Similarity	NPC265485
0.8649	High Similarity	NPC220939
0.8642	High Similarity	NPC6391
0.8642	High Similarity	NPC82979
0.863	High Similarity	NPC92801
0.8625	High Similarity	NPC231310
0.8625	High Similarity	NPC470077
0.8625	High Similarity	NPC185568
0.8625	High Similarity	NPC238485
0.8611	High Similarity	NPC208999
0.8611	High Similarity	NPC96484
0.8608	High Similarity	NPC304285
0.8608	High Similarity	NPC470049
0.8608	High Similarity	NPC202389
0.8608	High Similarity	NPC189972
0.8592	High Similarity	NPC476039
0.8592	High Similarity	NPC286669
0.8592	High Similarity	NPC202017
0.8592	High Similarity	NPC222366
0.859	High Similarity	NPC287749
0.8571	High Similarity	NPC300499
0.8571	High Similarity	NPC196753
0.8571	High Similarity	NPC473943
0.8571	High Similarity	NPC275910
0.8571	High Similarity	NPC98386
0.8571	High Similarity	NPC230295
0.8571	High Similarity	NPC158662
0.8571	High Similarity	NPC253807
0.8553	High Similarity	NPC240604
0.8553	High Similarity	NPC265328
0.8553	High Similarity	NPC106364
0.8553	High Similarity	NPC134330
0.8553	High Similarity	NPC120098
0.8553	High Similarity	NPC129165
0.8553	High Similarity	NPC290598
0.8553	High Similarity	NPC122418
0.8553	High Similarity	NPC113733
0.8553	High Similarity	NPC30590
0.8553	High Similarity	NPC477925
0.8553	High Similarity	NPC107059
0.8553	High Similarity	NPC27765
0.8553	High Similarity	NPC189883
0.8553	High Similarity	NPC300324
0.8553	High Similarity	NPC321381
0.8553	High Similarity	NPC321016
0.8553	High Similarity	NPC274079
0.8537	High Similarity	NPC149224
0.8533	High Similarity	NPC469534
0.8533	High Similarity	NPC469593
0.8533	High Similarity	NPC469533
0.8519	High Similarity	NPC470360
0.8519	High Similarity	NPC318390
0.8519	High Similarity	NPC157257
0.8519	High Similarity	NPC266511
0.8514	High Similarity	NPC477792
0.8514	High Similarity	NPC23954
0.85	High Similarity	NPC237795
0.85	High Similarity	NPC82623
0.85	High Similarity	NPC474634
0.85	High Similarity	NPC82538
0.85	High Similarity	NPC475789
0.8493	Intermediate Similarity	NPC9942
0.8493	Intermediate Similarity	NPC474248
0.8481	Intermediate Similarity	NPC474683
0.8481	Intermediate Similarity	NPC474759
0.8481	Intermediate Similarity	NPC82986
0.8481	Intermediate Similarity	NPC474752
0.8481	Intermediate Similarity	NPC7505
0.8481	Intermediate Similarity	NPC159148
0.8481	Intermediate Similarity	NPC474731
0.8481	Intermediate Similarity	NPC142163
0.8481	Intermediate Similarity	NPC474531
0.8462	Intermediate Similarity	NPC1319
0.8462	Intermediate Similarity	NPC472463
0.8462	Intermediate Similarity	NPC100906
0.8452	Intermediate Similarity	NPC3345
0.8452	Intermediate Similarity	NPC329596
0.8452	Intermediate Similarity	NPC80561
0.8452	Intermediate Similarity	NPC295668
0.8452	Intermediate Similarity	NPC11216
0.8452	Intermediate Similarity	NPC291484
0.8452	Intermediate Similarity	NPC204188
0.8442	Intermediate Similarity	NPC198968
0.8442	Intermediate Similarity	NPC318495
0.8442	Intermediate Similarity	NPC214570
0.8442	Intermediate Similarity	NPC155986
0.8434	Intermediate Similarity	NPC133588
0.8434	Intermediate Similarity	NPC188896
0.8421	Intermediate Similarity	NPC134847
0.8421	Intermediate Similarity	NPC313179
0.8421	Intermediate Similarity	NPC141071
0.8421	Intermediate Similarity	NPC22105
0.8421	Intermediate Similarity	NPC69383
0.8421	Intermediate Similarity	NPC136188
0.8421	Intermediate Similarity	NPC257347
0.8421	Intermediate Similarity	NPC171148
0.8421	Intermediate Similarity	NPC471723
0.8421	Intermediate Similarity	NPC28657
0.8421	Intermediate Similarity	NPC138374
0.8421	Intermediate Similarity	NPC230301
0.8421	Intermediate Similarity	NPC285893
0.8421	Intermediate Similarity	NPC304309
0.8421	Intermediate Similarity	NPC34700
0.8421	Intermediate Similarity	NPC162742
0.8421	Intermediate Similarity	NPC288035
0.8415	Intermediate Similarity	NPC299068
0.8415	Intermediate Similarity	NPC470955
0.84	Intermediate Similarity	NPC68443
0.84	Intermediate Similarity	NPC130665
0.84	Intermediate Similarity	NPC474743
0.8395	Intermediate Similarity	NPC474047
0.8375	Intermediate Similarity	NPC248886
0.8375	Intermediate Similarity	NPC471408
0.8375	Intermediate Similarity	NPC155521
0.8356	Intermediate Similarity	NPC471238
0.8356	Intermediate Similarity	NPC32055
0.8354	Intermediate Similarity	NPC281880

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 NPC91594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1526
0.2-0.3	3976
0.3-0.4	2344
0.4-0.5	713
0.5-0.6	234
0.6-0.7	142
0.7-0.8	46
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
0.8462	Intermediate Similarity	NPD7645	Phase 2
0.8421	Intermediate Similarity	NPD8264	Approved
0.8421	Intermediate Similarity	NPD7339	Approved
0.8421	Intermediate Similarity	NPD6942	Approved
0.8312	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7525	Registered
0.7882	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4784	Approved
0.7821	Intermediate Similarity	NPD6926	Approved
0.7821	Intermediate Similarity	NPD6924	Approved
0.7821	Intermediate Similarity	NPD4785	Approved
0.7778	Intermediate Similarity	NPD6929	Approved
0.7738	Intermediate Similarity	NPD4786	Approved
0.7711	Intermediate Similarity	NPD3667	Approved
0.7683	Intermediate Similarity	NPD6931	Approved
0.7683	Intermediate Similarity	NPD6930	Phase 2
0.7683	Intermediate Similarity	NPD7514	Phase 3
0.7683	Intermediate Similarity	NPD7332	Phase 2
0.7662	Intermediate Similarity	NPD7143	Approved
0.7662	Intermediate Similarity	NPD7144	Approved
0.7654	Intermediate Similarity	NPD7145	Approved
0.7625	Intermediate Similarity	NPD6933	Approved
0.759	Intermediate Similarity	NPD6902	Approved
0.7564	Intermediate Similarity	NPD4243	Approved
0.7564	Intermediate Similarity	NPD7152	Approved
0.7564	Intermediate Similarity	NPD7150	Approved
0.7564	Intermediate Similarity	NPD7151	Approved
0.7558	Intermediate Similarity	NPD3618	Phase 1
0.7534	Intermediate Similarity	NPD368	Approved
0.7532	Intermediate Similarity	NPD6922	Approved
0.7532	Intermediate Similarity	NPD6923	Approved
0.7531	Intermediate Similarity	NPD5776	Phase 2
0.7531	Intermediate Similarity	NPD6925	Approved
0.7528	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.747	Intermediate Similarity	NPD7509	Discontinued
0.7412	Intermediate Similarity	NPD6695	Phase 3
0.7333	Intermediate Similarity	NPD7515	Phase 2
0.7326	Intermediate Similarity	NPD3665	Phase 1
0.7326	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3666	Approved
0.7326	Intermediate Similarity	NPD3133	Approved
0.7317	Intermediate Similarity	NPD6932	Approved
0.7262	Intermediate Similarity	NPD4748	Discontinued
0.7241	Intermediate Similarity	NPD6893	Approved
0.7183	Intermediate Similarity	NPD342	Phase 1
0.7176	Intermediate Similarity	NPD6898	Phase 1
0.7159	Intermediate Similarity	NPD4623	Approved
0.7159	Intermediate Similarity	NPD4519	Discontinued
0.7158	Intermediate Similarity	NPD7640	Approved
0.7158	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD4195	Approved
0.7079	Intermediate Similarity	NPD7750	Discontinued
0.7079	Intermediate Similarity	NPD7524	Approved
0.7073	Intermediate Similarity	NPD4190	Phase 3
0.7073	Intermediate Similarity	NPD5275	Approved
0.7065	Intermediate Similarity	NPD4202	Approved
0.7053	Intermediate Similarity	NPD7638	Approved
0.7021	Intermediate Similarity	NPD5221	Approved
0.7021	Intermediate Similarity	NPD5222	Approved
0.7021	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5211	Phase 2
0.6989	Remote Similarity	NPD7748	Approved
0.6947	Remote Similarity	NPD5173	Approved
0.6941	Remote Similarity	NPD6683	Phase 2
0.6932	Remote Similarity	NPD3668	Phase 3
0.6882	Remote Similarity	NPD6399	Phase 3
0.6875	Remote Similarity	NPD5290	Discontinued
0.6875	Remote Similarity	NPD4225	Approved
0.6869	Remote Similarity	NPD5141	Approved
0.686	Remote Similarity	NPD4695	Discontinued
0.6854	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4219	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6804	Remote Similarity	NPD5286	Approved
0.6804	Remote Similarity	NPD4696	Approved
0.6804	Remote Similarity	NPD5285	Approved
0.6778	Remote Similarity	NPD5279	Phase 3
0.6774	Remote Similarity	NPD7637	Suspended
0.6774	Remote Similarity	NPD6411	Approved
0.6774	Remote Similarity	NPD7087	Discontinued
0.6771	Remote Similarity	NPD4755	Approved
0.6771	Remote Similarity	NPD7902	Approved
0.6739	Remote Similarity	NPD6051	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6735	Remote Similarity	NPD5223	Approved
0.6705	Remote Similarity	NPD4221	Approved
0.6705	Remote Similarity	NPD4223	Phase 3
0.6702	Remote Similarity	NPD5779	Approved
0.6702	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD7136	Phase 2
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6633	Remote Similarity	NPD4700	Approved
0.6627	Remote Similarity	NPD4732	Discontinued
0.66	Remote Similarity	NPD5174	Approved
0.66	Remote Similarity	NPD5175	Approved
0.6593	Remote Similarity	NPD7334	Approved
0.6593	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7521	Approved
0.6593	Remote Similarity	NPD5330	Approved
0.6593	Remote Similarity	NPD6409	Approved
0.6593	Remote Similarity	NPD7146	Approved
0.6593	Remote Similarity	NPD6684	Approved
0.6566	Remote Similarity	NPD4159	Approved
0.6562	Remote Similarity	NPD4629	Approved
0.6562	Remote Similarity	NPD5210	Approved
0.6559	Remote Similarity	NPD6101	Approved
0.6559	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4197	Approved
0.6505	Remote Similarity	NPD6881	Approved
0.6505	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.6484	Remote Similarity	NPD1696	Phase 3
0.6477	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6463	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7900	Approved
0.6452	Remote Similarity	NPD6903	Approved
0.6452	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4788	Approved
0.6437	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3617	Approved
0.6436	Remote Similarity	NPD4754	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6413	Remote Similarity	NPD4138	Approved
0.6413	Remote Similarity	NPD4689	Approved
0.6413	Remote Similarity	NPD4693	Phase 3
0.6413	Remote Similarity	NPD4688	Approved
0.6413	Remote Similarity	NPD4690	Approved
0.6413	Remote Similarity	NPD5690	Phase 2
0.6413	Remote Similarity	NPD5205	Approved
0.6408	Remote Similarity	NPD5697	Approved
0.6383	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7290	Approved
0.6381	Remote Similarity	NPD6883	Approved
0.6381	Remote Similarity	NPD7102	Approved
0.6374	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6011	Approved
0.6346	Remote Similarity	NPD5168	Approved
0.6346	Remote Similarity	NPD4729	Approved
0.6346	Remote Similarity	NPD4730	Approved
0.6346	Remote Similarity	NPD7320	Approved
0.6344	Remote Similarity	NPD3573	Approved
0.6321	Remote Similarity	NPD6617	Approved
0.6321	Remote Similarity	NPD6869	Approved
0.6321	Remote Similarity	NPD6847	Approved
0.6321	Remote Similarity	NPD6649	Approved
0.6321	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD8130	Phase 1
0.6311	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD4768	Approved
0.6304	Remote Similarity	NPD1694	Approved
0.6292	Remote Similarity	NPD4821	Approved
0.6292	Remote Similarity	NPD4819	Approved
0.6292	Remote Similarity	NPD4822	Approved
0.6292	Remote Similarity	NPD4820	Approved
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6014	Approved
0.6286	Remote Similarity	NPD6012	Approved
0.6286	Remote Similarity	NPD6013	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6277	Remote Similarity	NPD4722	Approved
0.6277	Remote Similarity	NPD6672	Approved
0.6277	Remote Similarity	NPD4723	Approved
0.6277	Remote Similarity	NPD5737	Approved
0.6264	Remote Similarity	NPD5331	Approved
0.6264	Remote Similarity	NPD5332	Approved
0.6264	Remote Similarity	NPD5362	Discontinued
0.6262	Remote Similarity	NPD8297	Approved
0.6262	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD8034	Phase 2
0.625	Remote Similarity	NPD5701	Approved
0.6238	Remote Similarity	NPD5344	Discontinued
0.6237	Remote Similarity	NPD4694	Approved
0.6237	Remote Similarity	NPD5280	Approved
0.6226	Remote Similarity	NPD5135	Approved
0.6226	Remote Similarity	NPD5249	Phase 3
0.6226	Remote Similarity	NPD5251	Approved
0.6226	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5248	Approved
0.6226	Remote Similarity	NPD5250	Approved
0.6226	Remote Similarity	NPD4634	Approved
0.6226	Remote Similarity	NPD5169	Approved
0.6226	Remote Similarity	NPD5247	Approved
0.6222	Remote Similarity	NPD4790	Discontinued
0.619	Remote Similarity	NPD4787	Phase 1

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