NPASS Compound

Structure

NPC185587 OpenBabel07101718182D 23 24 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 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 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 2 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 23 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 16 17 1 0 0 0 0 17 21 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 21 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.26
Volume:	364.33
LogP:	5.996
LogD:	5.188
LogS:	-5.751
# Rotatable Bonds:	5
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	4.001
Fsp3:	0.762
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.738
MDCK Permeability:	2.0524452338577248e-05
Pgp-inhibitor:	0.509
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.879
30% Bioavailability (F30%):	0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	93.3799819946289%
Volume Distribution (VD):	1.133
Pgp-substrate:	4.596007347106934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.204
CYP1A2-substrate:	0.292
CYP2C19-inhibitor:	0.425
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.462
CYP2C9-substrate:	0.719
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.63
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	5.137
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.156
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.586
Skin Sensitization:	0.831
Carcinogencity:	0.048
Eye Corrosion:	0.93
Eye Irritation:	0.974
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC185587

Natural Product ID:	NPC185587
*Common Name:**	Methyl Copalate
IUPAC Name:	methyl (E)-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoate
Synonyms:	Methyl Copalate
Standard InCHIKey:	KYTKOCVFNCZSSC-PSLIWGKLSA-N
Standard InCHI:	InChI=1S/C21H34O2/c1-15(14-19(22)23-6)8-10-17-16(2)9-11-18-20(3,4)12-7-13-21(17,18)5/h14,17-18H,2,7-13H2,1,3-6H3/b15-14+/t17-,18-,21+/m1/s1
SMILES:	COC(=O)/C=C(/CC[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CCCC2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048913
PubChem CID:	13858180
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
NPO32774	Copaifera	Genus	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22440015]

☑ 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
IC50	2
Others	12

Activity Type	# Activity
Cell Line	1
Organism	12
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2679	Cell Line	LLC-MK2	Macaca mulatta	CC50	=	69100.0	nM	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	83300.0	nM	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	EC50	=	377300.0	nM	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	2500.0	nM	PMID[485790]
NPT27	Others	Unspecified		HC50	=	1597.0	uM	PMID[485790]
NPT27	Others	Unspecified		Ratio CC50/IC50	=	27.6	n.a.	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	38.0	%	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	85.91	%	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	9.22	%	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	2.25	%	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	2.62	%	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	0.66	%	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	0.21	%	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	98.49	%	PMID[485790]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	0.64	%	PMID[485790]

☑ 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 NPC185587 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	176
0.1-0.2	1717
0.2-0.3	9228
0.3-0.4	15948
0.4-0.5	8374
0.5-0.6	5583
0.6-0.7	1462
0.7-0.8	187
0.8-0.85	15
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC329698
0.8906	High Similarity	NPC107258
0.8696	High Similarity	NPC20025
0.8571	High Similarity	NPC65650
0.8485	Intermediate Similarity	NPC259156
0.8485	Intermediate Similarity	NPC242945
0.8472	Intermediate Similarity	NPC105197
0.8451	Intermediate Similarity	NPC4509
0.8406	Intermediate Similarity	NPC181587
0.8356	Intermediate Similarity	NPC190211
0.8133	Intermediate Similarity	NPC40228
0.8028	Intermediate Similarity	NPC144947
0.7937	Intermediate Similarity	NPC96663
0.7922	Intermediate Similarity	NPC469
0.7922	Intermediate Similarity	NPC474976
0.7922	Intermediate Similarity	NPC42476
0.7922	Intermediate Similarity	NPC474790
0.791	Intermediate Similarity	NPC226066
0.7887	Intermediate Similarity	NPC133253
0.7821	Intermediate Similarity	NPC96055
0.7821	Intermediate Similarity	NPC318515
0.7792	Intermediate Similarity	NPC16321
0.7792	Intermediate Similarity	NPC200513
0.7792	Intermediate Similarity	NPC94200
0.7792	Intermediate Similarity	NPC471218
0.7778	Intermediate Similarity	NPC276336
0.7763	Intermediate Similarity	NPC469802
0.7722	Intermediate Similarity	NPC474013
0.7722	Intermediate Similarity	NPC329630
0.7722	Intermediate Similarity	NPC30984
0.7703	Intermediate Similarity	NPC474463
0.7692	Intermediate Similarity	NPC472440
0.7692	Intermediate Similarity	NPC311070
0.7692	Intermediate Similarity	NPC60772
0.7692	Intermediate Similarity	NPC477124
0.7662	Intermediate Similarity	NPC229584
0.7662	Intermediate Similarity	NPC14203
0.7662	Intermediate Similarity	NPC170303
0.7647	Intermediate Similarity	NPC169275
0.7647	Intermediate Similarity	NPC52449
0.7639	Intermediate Similarity	NPC21944
0.7639	Intermediate Similarity	NPC257618
0.7632	Intermediate Similarity	NPC242767
0.76	Intermediate Similarity	NPC189206
0.76	Intermediate Similarity	NPC132542
0.7564	Intermediate Similarity	NPC268122
0.7534	Intermediate Similarity	NPC476489
0.7534	Intermediate Similarity	NPC222244
0.7534	Intermediate Similarity	NPC109576
0.7534	Intermediate Similarity	NPC180015
0.7534	Intermediate Similarity	NPC476490
0.7534	Intermediate Similarity	NPC56747
0.7534	Intermediate Similarity	NPC16349
0.7534	Intermediate Similarity	NPC130016
0.7532	Intermediate Similarity	NPC281880
0.7532	Intermediate Similarity	NPC233332
0.75	Intermediate Similarity	NPC86316
0.75	Intermediate Similarity	NPC472442
0.75	Intermediate Similarity	NPC217394
0.75	Intermediate Similarity	NPC106416
0.75	Intermediate Similarity	NPC65661
0.7468	Intermediate Similarity	NPC118423
0.7468	Intermediate Similarity	NPC476927
0.7467	Intermediate Similarity	NPC19907
0.7439	Intermediate Similarity	NPC93411
0.7439	Intermediate Similarity	NPC474629
0.7436	Intermediate Similarity	NPC159148
0.7436	Intermediate Similarity	NPC25554
0.7432	Intermediate Similarity	NPC166797
0.7432	Intermediate Similarity	NPC168975
0.7432	Intermediate Similarity	NPC75485
0.7432	Intermediate Similarity	NPC238146
0.7429	Intermediate Similarity	NPC255781
0.7407	Intermediate Similarity	NPC220478
0.7407	Intermediate Similarity	NPC131813
0.7375	Intermediate Similarity	NPC306951
0.7375	Intermediate Similarity	NPC470800
0.7368	Intermediate Similarity	NPC54996
0.7368	Intermediate Similarity	NPC472300
0.7368	Intermediate Similarity	NPC61952
0.7353	Intermediate Similarity	NPC326645
0.7353	Intermediate Similarity	NPC317177
0.7353	Intermediate Similarity	NPC317025
0.7353	Intermediate Similarity	NPC329416
0.7349	Intermediate Similarity	NPC174342
0.7349	Intermediate Similarity	NPC177141
0.7349	Intermediate Similarity	NPC471654
0.7349	Intermediate Similarity	NPC474844
0.7342	Intermediate Similarity	NPC256112
0.7342	Intermediate Similarity	NPC2524
0.7333	Intermediate Similarity	NPC476346
0.7324	Intermediate Similarity	NPC472266
0.7317	Intermediate Similarity	NPC477228
0.7317	Intermediate Similarity	NPC75315
0.7317	Intermediate Similarity	NPC163016
0.7308	Intermediate Similarity	NPC268827
0.7284	Intermediate Similarity	NPC189311
0.7284	Intermediate Similarity	NPC42586
0.7284	Intermediate Similarity	NPC473251
0.7273	Intermediate Similarity	NPC184737
0.7273	Intermediate Similarity	NPC198240
0.7273	Intermediate Similarity	NPC470052
0.7273	Intermediate Similarity	NPC11130
0.7273	Intermediate Similarity	NPC239098
0.7262	Intermediate Similarity	NPC78973
0.7262	Intermediate Similarity	NPC101651
0.7262	Intermediate Similarity	NPC159748
0.7262	Intermediate Similarity	NPC476369
0.7262	Intermediate Similarity	NPC476437
0.7262	Intermediate Similarity	NPC273199
0.726	Intermediate Similarity	NPC469660
0.725	Intermediate Similarity	NPC12283
0.725	Intermediate Similarity	NPC22611
0.725	Intermediate Similarity	NPC30502
0.725	Intermediate Similarity	NPC474193
0.7246	Intermediate Similarity	NPC155849
0.7237	Intermediate Similarity	NPC27205
0.7237	Intermediate Similarity	NPC40353
0.7229	Intermediate Similarity	NPC472810
0.7229	Intermediate Similarity	NPC472809
0.7229	Intermediate Similarity	NPC472302
0.7229	Intermediate Similarity	NPC106332
0.7222	Intermediate Similarity	NPC476945
0.7195	Intermediate Similarity	NPC471219
0.7195	Intermediate Similarity	NPC118266
0.7195	Intermediate Similarity	NPC168248
0.7183	Intermediate Similarity	NPC81907
0.7183	Intermediate Similarity	NPC116013
0.7176	Intermediate Similarity	NPC329842
0.716	Intermediate Similarity	NPC149869
0.716	Intermediate Similarity	NPC475100
0.7143	Intermediate Similarity	NPC79027
0.7143	Intermediate Similarity	NPC284561
0.7143	Intermediate Similarity	NPC50488
0.7143	Intermediate Similarity	NPC316500
0.7143	Intermediate Similarity	NPC34883
0.7143	Intermediate Similarity	NPC474396
0.7143	Intermediate Similarity	NPC262747
0.7143	Intermediate Similarity	NPC470557
0.7143	Intermediate Similarity	NPC251528
0.7143	Intermediate Similarity	NPC473756
0.7125	Intermediate Similarity	NPC469805
0.7125	Intermediate Similarity	NPC472867
0.7125	Intermediate Similarity	NPC186276
0.7125	Intermediate Similarity	NPC472239
0.7125	Intermediate Similarity	NPC469804
0.7108	Intermediate Similarity	NPC166857
0.7108	Intermediate Similarity	NPC125925
0.7097	Intermediate Similarity	NPC22765
0.7093	Intermediate Similarity	NPC7349
0.7093	Intermediate Similarity	NPC472871
0.7093	Intermediate Similarity	NPC53555
0.7089	Intermediate Similarity	NPC195424
0.7089	Intermediate Similarity	NPC10636
0.7083	Intermediate Similarity	NPC176107
0.7083	Intermediate Similarity	NPC69649
0.7083	Intermediate Similarity	NPC68703
0.7083	Intermediate Similarity	NPC254886
0.7073	Intermediate Similarity	NPC471795
0.7073	Intermediate Similarity	NPC35933
0.7059	Intermediate Similarity	NPC221111
0.7059	Intermediate Similarity	NPC280149
0.7059	Intermediate Similarity	NPC8062
0.7059	Intermediate Similarity	NPC51486
0.7059	Intermediate Similarity	NPC310479
0.7059	Intermediate Similarity	NPC182136
0.7059	Intermediate Similarity	NPC477782
0.7051	Intermediate Similarity	NPC209135
0.7051	Intermediate Similarity	NPC59436
0.7051	Intermediate Similarity	NPC471220
0.7051	Intermediate Similarity	NPC474816
0.7049	Intermediate Similarity	NPC128280
0.7037	Intermediate Similarity	NPC3856
0.7037	Intermediate Similarity	NPC279639
0.7037	Intermediate Similarity	NPC193198
0.7037	Intermediate Similarity	NPC79945
0.7037	Intermediate Similarity	NPC23748
0.7037	Intermediate Similarity	NPC49208
0.7027	Intermediate Similarity	NPC37929
0.7027	Intermediate Similarity	NPC64234
0.7024	Intermediate Similarity	NPC196407
0.7024	Intermediate Similarity	NPC472870
0.7024	Intermediate Similarity	NPC473879
0.7024	Intermediate Similarity	NPC226863
0.7013	Intermediate Similarity	NPC473223
0.7013	Intermediate Similarity	NPC899
0.7011	Intermediate Similarity	NPC476415
0.7011	Intermediate Similarity	NPC140277
0.7011	Intermediate Similarity	NPC469697
0.7011	Intermediate Similarity	NPC324078
0.7011	Intermediate Similarity	NPC477722
0.7011	Intermediate Similarity	NPC105490
0.6988	Remote Similarity	NPC472863
0.6988	Remote Similarity	NPC286153
0.6988	Remote Similarity	NPC475069
0.6988	Remote Similarity	NPC329692
0.6988	Remote Similarity	NPC175145
0.6986	Remote Similarity	NPC155198
0.6977	Remote Similarity	NPC472814
0.6977	Remote Similarity	NPC477783

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 NPC185587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1815
0.2-0.3	4599
0.3-0.4	1945
0.4-0.5	367
0.5-0.6	213
0.6-0.7	48
0.7-0.8	2
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
0.791	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4193	Approved
0.7353	Intermediate Similarity	NPD4194	Approved
0.7353	Intermediate Similarity	NPD4191	Approved
0.7353	Intermediate Similarity	NPD4192	Approved
0.7042	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6051	Approved
0.6892	Remote Similarity	NPD4137	Phase 3
0.6883	Remote Similarity	NPD8039	Approved
0.68	Remote Similarity	NPD4747	Approved
0.68	Remote Similarity	NPD4691	Approved
0.6786	Remote Similarity	NPD7521	Approved
0.6786	Remote Similarity	NPD7334	Approved
0.6786	Remote Similarity	NPD6684	Approved
0.6786	Remote Similarity	NPD7146	Approved
0.6786	Remote Similarity	NPD5330	Approved
0.6786	Remote Similarity	NPD6409	Approved
0.6747	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7638	Approved
0.663	Remote Similarity	NPD7640	Approved
0.663	Remote Similarity	NPD7639	Approved
0.6628	Remote Similarity	NPD5737	Approved
0.6628	Remote Similarity	NPD6672	Approved
0.6628	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6903	Approved
0.6591	Remote Similarity	NPD5693	Phase 1
0.6538	Remote Similarity	NPD4058	Approved
0.6538	Remote Similarity	NPD5733	Approved
0.6522	Remote Similarity	NPD4225	Approved
0.6494	Remote Similarity	NPD5276	Approved
0.6471	Remote Similarity	NPD1694	Approved
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD6927	Phase 3
0.6364	Remote Similarity	NPD6904	Approved
0.6329	Remote Similarity	NPD4687	Approved
0.6322	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5209	Approved
0.6264	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7748	Approved
0.6264	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD5208	Approved
0.6222	Remote Similarity	NPD7515	Phase 2
0.6222	Remote Similarity	NPD7637	Suspended
0.6207	Remote Similarity	NPD6098	Approved
0.6197	Remote Similarity	NPD287	Approved
0.6196	Remote Similarity	NPD6049	Phase 2
0.6196	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6686	Approved
0.6145	Remote Similarity	NPD4195	Approved
0.6143	Remote Similarity	NPD4219	Approved
0.6092	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4695	Discontinued
0.6064	Remote Similarity	NPD6083	Phase 2
0.6064	Remote Similarity	NPD6084	Phase 2
0.6064	Remote Similarity	NPD7902	Approved
0.6049	Remote Similarity	NPD8264	Approved
0.6044	Remote Similarity	NPD6050	Approved
0.6026	Remote Similarity	NPD6922	Approved
0.6026	Remote Similarity	NPD6923	Approved
0.6024	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4519	Discontinued
0.6023	Remote Similarity	NPD4623	Approved
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8028	Phase 2
0.5979	Remote Similarity	NPD7632	Discontinued
0.5978	Remote Similarity	NPD6399	Phase 3
0.5977	Remote Similarity	NPD3133	Approved
0.5977	Remote Similarity	NPD3665	Phase 1
0.5977	Remote Similarity	NPD3666	Approved
0.5957	Remote Similarity	NPD7732	Phase 3
0.5952	Remote Similarity	NPD7645	Phase 2
0.5949	Remote Similarity	NPD7143	Approved
0.5949	Remote Similarity	NPD7144	Approved
0.5934	Remote Similarity	NPD5785	Approved
0.5934	Remote Similarity	NPD5692	Phase 3
0.5934	Remote Similarity	NPD5207	Approved
0.593	Remote Similarity	NPD4221	Approved
0.593	Remote Similarity	NPD4223	Phase 3
0.5926	Remote Similarity	NPD6924	Approved
0.5926	Remote Similarity	NPD6926	Approved
0.5914	Remote Similarity	NPD6001	Approved
0.5909	Remote Similarity	NPD5329	Approved
0.5904	Remote Similarity	NPD5776	Phase 2
0.5904	Remote Similarity	NPD6925	Approved
0.5882	Remote Similarity	NPD7332	Phase 2
0.5882	Remote Similarity	NPD7514	Phase 3
0.5875	Remote Similarity	NPD7152	Approved
0.5875	Remote Similarity	NPD7150	Approved
0.5875	Remote Similarity	NPD7151	Approved
0.5875	Remote Similarity	NPD4243	Approved
0.5873	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5694	Approved
0.5862	Remote Similarity	NPD3971	Phase 1
0.5854	Remote Similarity	NPD7339	Approved
0.5854	Remote Similarity	NPD6942	Approved
0.5851	Remote Similarity	NPD5695	Phase 3
0.5843	Remote Similarity	NPD3618	Phase 1
0.5833	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7145	Approved
0.5833	Remote Similarity	NPD5696	Approved
0.5824	Remote Similarity	NPD5328	Approved
0.5821	Remote Similarity	NPD8262	Approved
0.5821	Remote Similarity	NPD4220	Pre-registration
0.5814	Remote Similarity	NPD6902	Approved
0.5795	Remote Similarity	NPD4786	Approved
0.5795	Remote Similarity	NPD4197	Approved
0.5783	Remote Similarity	NPD6933	Approved
0.5783	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6648	Approved
0.5773	Remote Similarity	NPD6404	Discontinued
0.5765	Remote Similarity	NPD6929	Approved
0.5761	Remote Similarity	NPD46	Approved
0.5761	Remote Similarity	NPD6698	Approved
0.5747	Remote Similarity	NPD3667	Approved
0.5732	Remote Similarity	NPD4784	Approved
0.5732	Remote Similarity	NPD4785	Approved
0.573	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6932	Approved
0.5714	Remote Similarity	NPD5344	Discontinued
0.5701	Remote Similarity	NPD7115	Discovery
0.5699	Remote Similarity	NPD6079	Approved
0.5699	Remote Similarity	NPD5284	Approved
0.5699	Remote Similarity	NPD5281	Approved
0.5698	Remote Similarity	NPD6931	Approved
0.5698	Remote Similarity	NPD6930	Phase 2
0.5698	Remote Similarity	NPD7525	Registered
0.5682	Remote Similarity	NPD6695	Phase 3
0.5682	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.567	Remote Similarity	NPD5926	Approved
0.5667	Remote Similarity	NPD4689	Approved
0.5667	Remote Similarity	NPD4693	Phase 3
0.5667	Remote Similarity	NPD5205	Approved
0.5667	Remote Similarity	NPD4690	Approved
0.5667	Remote Similarity	NPD5279	Phase 3
0.5667	Remote Similarity	NPD4138	Approved
0.5667	Remote Similarity	NPD4688	Approved
0.5652	Remote Similarity	NPD4753	Phase 2
0.5648	Remote Similarity	NPD7328	Approved
0.5648	Remote Similarity	NPD7327	Approved
0.5647	Remote Similarity	NPD3617	Approved
0.5644	Remote Similarity	NPD6675	Approved
0.5644	Remote Similarity	NPD5739	Approved
0.5644	Remote Similarity	NPD6402	Approved
0.5644	Remote Similarity	NPD7128	Approved
0.5632	Remote Similarity	NPD6898	Phase 1
0.5625	Remote Similarity	NPD7614	Phase 1
0.5618	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD3668	Phase 3
0.56	Remote Similarity	NPD6052	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