NPASS Compound

Structure

CID321505 OpenBabel06191716152D 22 24 0 0 1 0 0 0 0 0999 V2000 3.4641 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 3.4641 1.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 6.0622 2.5000 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 2.5981 1.5000 0.0000 C 0 0 3 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 22 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.15
Volume:	315.764
LogP:	2.186
LogD:	2.787
LogS:	-1.809
# Rotatable Bonds:	3
TPSA:	52.93
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.915
Synthetic Accessibility Score:	2.705
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.603
MDCK Permeability:	1.2755574061884545e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.112
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.209

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	67.5562744140625%
Volume Distribution (VD):	2.116
Pgp-substrate:	24.630699157714844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.261
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.192
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.786
CYP2D6-inhibitor:	0.678
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.855

ADMET: Excretion

Clearance (CL):	17.226
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.584
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.306
Rat Oral Acute Toxicity:	0.575
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.917
Carcinogencity:	0.097
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.691

Download Data

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

Natural Product: NPC321505

Natural Product ID:	NPC321505
*Common Name:**	Methyl Coclaurine
IUPAC Name:	1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Synonyms:	DL-N-methylcoclaurine
Standard InCHIKey:	BOKVLBSSPUTWLV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3
SMILES:	CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453292
PubChem CID:	2752274
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	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
IC50	2
Ki	2
Others	9

Activity Type	# Activity
CELL-LINE	4
Individual Protein	2
Protein Family	2
Tissue	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	73.6	%	PMID[554075]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	13.8	%	PMID[554075]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	24.8	%	PMID[554075]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	75.7	%	PMID[554075]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	70.8	%	PMID[554075]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	149.6	%	PMID[554075]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	106.6	%	PMID[554075]
NPT968	Protein Family	Adrenergic receptor alpha-1	Rattus norvegicus	Ki	=	2344.23	nM	PMID[554076]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Ki	=	22908.68	nM	PMID[554076]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	24547.09	nM	PMID[554076]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	67608.3	nM	PMID[554076]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	94.46	%	PMID[554077]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	96.63	%	PMID[554077]

☑ 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 NPC321505 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	263
0.1-0.2	1627
0.2-0.3	8593
0.3-0.4	9265
0.4-0.5	6050
0.5-0.6	11176
0.6-0.7	4216
0.7-0.8	1063
0.8-0.85	249
0.85-0.9	110
0.9-0.95	66
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC179825
1.0	High Similarity	NPC191376
0.9928	High Similarity	NPC24233
0.9928	High Similarity	NPC147390
0.9928	High Similarity	NPC246587
0.9928	High Similarity	NPC428
0.9928	High Similarity	NPC135538
0.9928	High Similarity	NPC476571
0.9855	High Similarity	NPC185838
0.9716	High Similarity	NPC477565
0.9716	High Similarity	NPC103379
0.9648	High Similarity	NPC88249
0.9648	High Similarity	NPC220858
0.9648	High Similarity	NPC97221
0.9648	High Similarity	NPC151895
0.9648	High Similarity	NPC192768
0.958	High Similarity	NPC277669
0.958	High Similarity	NPC76213
0.9574	High Similarity	NPC476151
0.9517	High Similarity	NPC276588
0.9517	High Similarity	NPC193949
0.9517	High Similarity	NPC184026
0.9517	High Similarity	NPC2413
0.9517	High Similarity	NPC5238
0.9517	High Similarity	NPC39701
0.9517	High Similarity	NPC295691
0.9517	High Similarity	NPC189266
0.9517	High Similarity	NPC110416
0.9517	High Similarity	NPC249797
0.9517	High Similarity	NPC54379
0.9517	High Similarity	NPC204828
0.9517	High Similarity	NPC278799
0.9517	High Similarity	NPC207757
0.9517	High Similarity	NPC172765
0.9517	High Similarity	NPC469817
0.9517	High Similarity	NPC127674
0.9493	High Similarity	NPC314682
0.9441	High Similarity	NPC207824
0.9441	High Similarity	NPC60538
0.9424	High Similarity	NPC474915
0.9424	High Similarity	NPC328750
0.9424	High Similarity	NPC188163
0.9424	High Similarity	NPC213206
0.9315	High Similarity	NPC477564
0.9315	High Similarity	NPC2295
0.9275	High Similarity	NPC131204
0.9275	High Similarity	NPC301050
0.9262	High Similarity	NPC166014
0.9262	High Similarity	NPC27410
0.9247	High Similarity	NPC82285
0.9247	High Similarity	NPC133011
0.9195	High Similarity	NPC111485
0.9189	High Similarity	NPC147091
0.9155	High Similarity	NPC128019
0.9155	High Similarity	NPC476567
0.9155	High Similarity	NPC136860
0.9091	High Similarity	NPC294249
0.9079	High Similarity	NPC238530
0.9079	High Similarity	NPC232514
0.9079	High Similarity	NPC276944
0.9034	High Similarity	NPC210437
0.9034	High Similarity	NPC476144
0.9034	High Similarity	NPC106295
0.9034	High Similarity	NPC51957
0.9034	High Similarity	NPC16107
0.902	High Similarity	NPC240841
0.902	High Similarity	NPC256012
0.902	High Similarity	NPC42549
0.902	High Similarity	NPC264850
0.902	High Similarity	NPC13916
0.902	High Similarity	NPC268503
0.902	High Similarity	NPC250846
0.902	High Similarity	NPC317272
0.9013	High Similarity	NPC324144
0.8986	High Similarity	NPC37272
0.898	High Similarity	NPC274026
0.8973	High Similarity	NPC475959
0.8973	High Similarity	NPC7467
0.8961	High Similarity	NPC81218
0.8961	High Similarity	NPC306555
0.8961	High Similarity	NPC158376
0.8961	High Similarity	NPC145832
0.8961	High Similarity	NPC117188
0.8961	High Similarity	NPC12053
0.8961	High Similarity	NPC205421
0.8961	High Similarity	NPC474931
0.8954	High Similarity	NPC306843
0.8954	High Similarity	NPC78222
0.8954	High Similarity	NPC13504
0.8954	High Similarity	NPC284183
0.8954	High Similarity	NPC253043
0.8954	High Similarity	NPC136508
0.8954	High Similarity	NPC96603
0.8954	High Similarity	NPC4138
0.8954	High Similarity	NPC24465
0.8954	High Similarity	NPC121275
0.8954	High Similarity	NPC196447
0.8954	High Similarity	NPC477563
0.8954	High Similarity	NPC212794
0.8933	High Similarity	NPC186063
0.8903	High Similarity	NPC204908
0.8903	High Similarity	NPC83198
0.8896	High Similarity	NPC81247
0.8896	High Similarity	NPC35627
0.8896	High Similarity	NPC476573
0.8889	High Similarity	NPC1229
0.8882	High Similarity	NPC205167
0.8882	High Similarity	NPC249274
0.8859	High Similarity	NPC26601
0.8841	High Similarity	NPC160193
0.8839	High Similarity	NPC210140
0.8824	High Similarity	NPC60186
0.8792	High Similarity	NPC81733
0.8792	High Similarity	NPC326316
0.8782	High Similarity	NPC66573
0.8767	High Similarity	NPC130926
0.875	High Similarity	NPC475326
0.8741	High Similarity	NPC170170
0.8741	High Similarity	NPC219233
0.8741	High Similarity	NPC211468
0.8734	High Similarity	NPC190783
0.8734	High Similarity	NPC152680
0.8734	High Similarity	NPC232386
0.8726	High Similarity	NPC168753
0.8726	High Similarity	NPC109925
0.8726	High Similarity	NPC118274
0.8718	High Similarity	NPC298979
0.871	High Similarity	NPC134858
0.8696	High Similarity	NPC172403
0.8681	High Similarity	NPC323123
0.8671	High Similarity	NPC475215
0.8671	High Similarity	NPC193528
0.8671	High Similarity	NPC253429
0.8671	High Similarity	NPC239775
0.8671	High Similarity	NPC108434
0.8667	High Similarity	NPC476568
0.8662	High Similarity	NPC470324
0.8658	High Similarity	NPC92541
0.8658	High Similarity	NPC219162
0.8645	High Similarity	NPC233650
0.8618	High Similarity	NPC138487
0.8618	High Similarity	NPC41178
0.8618	High Similarity	NPC216459
0.8616	High Similarity	NPC477020
0.8616	High Similarity	NPC66341
0.8616	High Similarity	NPC192135
0.8609	High Similarity	NPC233029
0.8609	High Similarity	NPC210148
0.8608	High Similarity	NPC477562
0.8608	High Similarity	NPC69712
0.8608	High Similarity	NPC26240
0.8571	High Similarity	NPC114364
0.8571	High Similarity	NPC320223
0.8571	High Similarity	NPC59028
0.8571	High Similarity	NPC92191
0.8562	High Similarity	NPC247639
0.8562	High Similarity	NPC128560
0.8562	High Similarity	NPC25084
0.8562	High Similarity	NPC199465
0.8562	High Similarity	NPC229166
0.8562	High Similarity	NPC146288
0.8535	High Similarity	NPC124657
0.8523	High Similarity	NPC253883
0.8523	High Similarity	NPC95075
0.8523	High Similarity	NPC90844
0.8523	High Similarity	NPC144863
0.8519	High Similarity	NPC32154
0.8516	High Similarity	NPC226428
0.8516	High Similarity	NPC215829
0.8516	High Similarity	NPC97072
0.8506	High Similarity	NPC476572
0.8497	Intermediate Similarity	NPC325871
0.8497	Intermediate Similarity	NPC80129
0.8497	Intermediate Similarity	NPC187022
0.8497	Intermediate Similarity	NPC99659
0.8481	Intermediate Similarity	NPC150879
0.8471	Intermediate Similarity	NPC3375
0.8471	Intermediate Similarity	NPC255607
0.8467	Intermediate Similarity	NPC130941
0.8466	Intermediate Similarity	NPC286119
0.8442	Intermediate Similarity	NPC126519
0.8442	Intermediate Similarity	NPC31311
0.8442	Intermediate Similarity	NPC234392
0.8442	Intermediate Similarity	NPC203784
0.8442	Intermediate Similarity	NPC170503
0.8438	Intermediate Similarity	NPC476331
0.8421	Intermediate Similarity	NPC476579
0.8415	Intermediate Similarity	NPC8836
0.8415	Intermediate Similarity	NPC15414
0.8415	Intermediate Similarity	NPC328155
0.8415	Intermediate Similarity	NPC271013
0.8415	Intermediate Similarity	NPC251735
0.8415	Intermediate Similarity	NPC42663
0.8415	Intermediate Similarity	NPC7715
0.8415	Intermediate Similarity	NPC279228
0.8415	Intermediate Similarity	NPC54654
0.8415	Intermediate Similarity	NPC285931
0.8415	Intermediate Similarity	NPC104196
0.8415	Intermediate Similarity	NPC182052
0.8415	Intermediate Similarity	NPC239824

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 NPC321505 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	750
0.2-0.3	1049
0.3-0.4	1674
0.4-0.5	2662
0.5-0.6	1820
0.6-0.7	737
0.7-0.8	237
0.8-0.85	29
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9424	High Similarity	NPD4664	Clinical (unspecified phase)
0.9034	High Similarity	NPD4584	Approved
0.8896	High Similarity	NPD4010	Discontinued
0.8792	High Similarity	NPD4017	Approved
0.8699	High Similarity	NPD5241	Discontinued
0.8675	High Similarity	NPD4773	Phase 2
0.8675	High Similarity	NPD4772	Phase 2
0.8662	High Similarity	NPD2898	Approved
0.8645	High Similarity	NPD7201	Clinical (unspecified phase)
0.8533	High Similarity	NPD3641	Approved
0.8533	High Similarity	NPD3640	Phase 3
0.8533	High Similarity	NPD3639	Approved
0.8523	High Similarity	NPD1754	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7298	Approved
0.8456	Intermediate Similarity	NPD2421	Approved
0.8456	Intermediate Similarity	NPD2420	Approved
0.8442	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD8054	Approved
0.8415	Intermediate Similarity	NPD8053	Approved
0.8411	Intermediate Similarity	NPD6030	Approved
0.8411	Intermediate Similarity	NPD6031	Approved
0.8397	Intermediate Similarity	NPD7831	Phase 2
0.8397	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7833	Phase 2
0.8389	Intermediate Similarity	NPD3845	Phase 1
0.838	Intermediate Similarity	NPD5718	Phase 2
0.8322	Intermediate Similarity	NPD2674	Phase 3
0.8313	Intermediate Similarity	NPD27	Approved
0.8313	Intermediate Similarity	NPD2489	Approved
0.831	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD2969	Approved
0.8137	Intermediate Similarity	NPD2970	Approved
0.8125	Intermediate Similarity	NPD3144	Approved
0.8125	Intermediate Similarity	NPD3145	Approved
0.8112	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6071	Discontinued
0.8075	Intermediate Similarity	NPD3051	Approved
0.8067	Intermediate Similarity	NPD5177	Phase 3
0.8061	Intermediate Similarity	NPD6297	Approved
0.8038	Intermediate Similarity	NPD2563	Approved
0.8038	Intermediate Similarity	NPD2560	Approved
0.8037	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD8099	Discontinued
0.7988	Intermediate Similarity	NPD8252	Approved
0.7988	Intermediate Similarity	NPD8251	Approved
0.7987	Intermediate Similarity	NPD6788	Approved
0.7974	Intermediate Similarity	NPD3124	Discontinued
0.7973	Intermediate Similarity	NPD6895	Approved
0.7973	Intermediate Similarity	NPD6896	Approved
0.7947	Intermediate Similarity	NPD3060	Approved
0.7939	Intermediate Similarity	NPD8156	Discontinued
0.7919	Intermediate Similarity	NPD1753	Discontinued
0.7902	Intermediate Similarity	NPD3053	Approved
0.7902	Intermediate Similarity	NPD3055	Approved
0.7901	Intermediate Similarity	NPD6107	Approved
0.7901	Intermediate Similarity	NPD7802	Discontinued
0.787	Intermediate Similarity	NPD6851	Approved
0.787	Intermediate Similarity	NPD6853	Approved
0.7862	Intermediate Similarity	NPD2978	Approved
0.7862	Intermediate Similarity	NPD2977	Approved
0.7853	Intermediate Similarity	NPD4166	Phase 2
0.7843	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7906	Approved
0.7834	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5978	Approved
0.7812	Intermediate Similarity	NPD5977	Approved
0.7811	Intermediate Similarity	NPD7311	Approved
0.7811	Intermediate Similarity	NPD4577	Approved
0.7811	Intermediate Similarity	NPD7312	Approved
0.7811	Intermediate Similarity	NPD7310	Approved
0.7811	Intermediate Similarity	NPD7313	Approved
0.7811	Intermediate Similarity	NPD4578	Approved
0.7811	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3110	Approved
0.777	Intermediate Similarity	NPD3109	Approved
0.7765	Intermediate Similarity	NPD7309	Approved
0.7755	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2667	Approved
0.773	Intermediate Similarity	NPD2668	Approved
0.7727	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD824	Approved
0.7712	Intermediate Similarity	NPD4162	Approved
0.7703	Intermediate Similarity	NPD4474	Approved
0.7703	Intermediate Similarity	NPD4475	Approved
0.7692	Intermediate Similarity	NPD2230	Approved
0.7692	Intermediate Similarity	NPD2232	Approved
0.7692	Intermediate Similarity	NPD2233	Approved
0.7674	Intermediate Similarity	NPD4663	Approved
0.7671	Intermediate Similarity	NPD3636	Approved
0.7671	Intermediate Similarity	NPD3637	Approved
0.7671	Intermediate Similarity	NPD3635	Approved
0.766	Intermediate Similarity	NPD4093	Discontinued
0.7654	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD2488	Approved
0.7644	Intermediate Similarity	NPD2490	Approved
0.7625	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7110	Phase 1
0.7619	Intermediate Similarity	NPD5312	Approved
0.7619	Intermediate Similarity	NPD5313	Approved
0.7613	Intermediate Similarity	NPD3692	Discontinued
0.761	Intermediate Similarity	NPD4005	Discontinued
0.7607	Intermediate Similarity	NPD4055	Discovery
0.7597	Intermediate Similarity	NPD4236	Phase 3
0.7597	Intermediate Similarity	NPD4237	Approved
0.7586	Intermediate Similarity	NPD5310	Approved
0.7586	Intermediate Similarity	NPD5311	Approved
0.7582	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4123	Phase 3
0.758	Intermediate Similarity	NPD1424	Approved
0.7571	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5155	Approved
0.7568	Intermediate Similarity	NPD5156	Approved
0.7564	Intermediate Similarity	NPD7124	Phase 2
0.755	Intermediate Similarity	NPD823	Approved
0.755	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD817	Approved
0.7548	Intermediate Similarity	NPD6331	Phase 2
0.7548	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4481	Phase 3
0.7533	Intermediate Similarity	NPD2238	Phase 2
0.7532	Intermediate Similarity	NPD6090	Discontinued
0.7517	Intermediate Similarity	NPD1669	Approved
0.75	Intermediate Similarity	NPD3594	Approved
0.75	Intermediate Similarity	NPD2605	Approved
0.75	Intermediate Similarity	NPD7281	Phase 3
0.75	Intermediate Similarity	NPD2606	Approved
0.75	Intermediate Similarity	NPD7280	Phase 3
0.75	Intermediate Similarity	NPD5604	Discontinued
0.75	Intermediate Similarity	NPD3595	Approved
0.7485	Intermediate Similarity	NPD6687	Approved
0.7485	Intermediate Similarity	NPD6688	Approved
0.7484	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6584	Phase 3
0.7483	Intermediate Similarity	NPD7905	Discontinued
0.7467	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD228	Approved
0.7436	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6748	Discontinued
0.7429	Intermediate Similarity	NPD7291	Discontinued
0.7423	Intermediate Similarity	NPD5773	Approved
0.7423	Intermediate Similarity	NPD5772	Approved
0.7421	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7037	Approved
0.7419	Intermediate Similarity	NPD7153	Discontinued
0.7415	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4098	Discontinued
0.7415	Intermediate Similarity	NPD4103	Phase 2
0.7403	Intermediate Similarity	NPD2161	Phase 2
0.7399	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4659	Approved
0.7389	Intermediate Similarity	NPD5160	Discontinued
0.7381	Intermediate Similarity	NPD4083	Discontinued
0.7375	Intermediate Similarity	NPD2122	Discontinued
0.7372	Intermediate Similarity	NPD6364	Approved
0.7372	Intermediate Similarity	NPD44	Approved
0.7368	Intermediate Similarity	NPD3920	Phase 2
0.7368	Intermediate Similarity	NPD7479	Phase 2
0.7362	Intermediate Similarity	NPD5720	Discontinued
0.7362	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7355	Intermediate Similarity	NPD3656	Approved
0.7351	Intermediate Similarity	NPD1130	Approved
0.7351	Intermediate Similarity	NPD1136	Approved
0.7351	Intermediate Similarity	NPD1132	Approved
0.7346	Intermediate Similarity	NPD4678	Approved
0.7346	Intermediate Similarity	NPD6876	Approved
0.7346	Intermediate Similarity	NPD6875	Approved
0.7346	Intermediate Similarity	NPD4675	Approved
0.7345	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5303	Approved
0.7343	Intermediate Similarity	NPD5304	Approved
0.7341	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4873	Discontinued
0.7305	Intermediate Similarity	NPD5677	Discontinued
0.7303	Intermediate Similarity	NPD3620	Phase 2
0.7303	Intermediate Similarity	NPD3062	Approved
0.7303	Intermediate Similarity	NPD3061	Approved
0.7303	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3059	Approved
0.7296	Intermediate Similarity	NPD7598	Phase 2
0.7285	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD598	Approved
0.7285	Intermediate Similarity	NPD597	Approved
0.7285	Intermediate Similarity	NPD601	Approved
0.7284	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6582	Phase 2
0.7279	Intermediate Similarity	NPD1420	Approved
0.7279	Intermediate Similarity	NPD6583	Phase 3
0.7279	Intermediate Similarity	NPD1421	Approved
0.7268	Intermediate Similarity	NPD2494	Approved
0.7268	Intermediate Similarity	NPD3452	Approved
0.7268	Intermediate Similarity	NPD3450	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