NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	271.12
Volume:	281.172
LogP:	0.453
LogD:	1.978
LogS:	-2.763
# Rotatable Bonds:	2
TPSA:	72.72
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	2.818
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.23
MDCK Permeability:	1.1181499758095015e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.835
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	53.823360443115234%
Volume Distribution (VD):	1.862
Pgp-substrate:	44.01987075805664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.171
CYP1A2-substrate:	0.881
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.645
CYP2D6-inhibitor:	0.546
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	19.162
Half-life (T1/2):	0.889

ADMET: Toxicity

hERG Blockers:	0.29
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.698
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.951
Carcinogencity:	0.134
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.696

Download Data

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

Natural Product: NPC219233

Natural Product ID:	NPC219233
*Common Name:**	(-)-Higenamine
IUPAC Name:	(1S)-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Synonyms:
Standard InCHIKey:	WZRCQWQRFZITDX-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2/t14-/m0/s1
SMILES:	Oc1ccc(cc1)C[C@@H]1NCCc2c1cc(O)c(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470491
PubChem CID:	440927
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
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	tuber	n.a.	PMID[12913245]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1293938]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16181762]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[18044843]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22223386]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Lateral roots	n.a.	n.a.	PMID[22607495]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22628040]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22907155]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23225552]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23707213]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23707213]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24170571]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24170571]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24190290]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24190290]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24793215]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[27761113]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[300080]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[300080]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30892884]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4893	Aconitum ciliare	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14688	Aconitum triphyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	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
IC50	5

Activity Type	# Activity
CELL-LINE	5
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4632	Individual Protein	Beta-2 adrenergic receptor	Rattus norvegicus	EC50	=	600.0	nM	PMID[468321]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	450000.0	nM	PMID[468320]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	>	1000000.0	nM	PMID[468320]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	1600.0	nM	PMID[468320]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	9100.0	nM	PMID[468320]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	25000.0	nM	PMID[468320]

☑ 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 NPC219233 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	281
0.1-0.2	1743
0.2-0.3	11224
0.3-0.4	6793
0.4-0.5	10798
0.5-0.6	9112
0.6-0.7	2141
0.7-0.8	487
0.8-0.85	75
0.85-0.9	17
0.9-0.95	16
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC170170
1.0	High Similarity	NPC211468
0.9924	High Similarity	NPC323123
0.9389	High Similarity	NPC33338
0.9389	High Similarity	NPC302171
0.9389	High Similarity	NPC300020
0.9155	High Similarity	NPC76213
0.9155	High Similarity	NPC277669
0.9077	High Similarity	NPC318965
0.9014	High Similarity	NPC207824
0.9014	High Similarity	NPC60538
0.8897	High Similarity	NPC477564
0.8897	High Similarity	NPC2295
0.8741	High Similarity	NPC321505
0.8741	High Similarity	NPC191376
0.8741	High Similarity	NPC179825
0.8681	High Similarity	NPC24233
0.8681	High Similarity	NPC428
0.8681	High Similarity	NPC476571
0.8681	High Similarity	NPC135538
0.8681	High Similarity	NPC147390
0.8681	High Similarity	NPC246587
0.8662	High Similarity	NPC294249
0.8601	High Similarity	NPC185838
0.8497	Intermediate Similarity	NPC35627
0.8497	Intermediate Similarity	NPC476573
0.8497	Intermediate Similarity	NPC81247
0.8493	Intermediate Similarity	NPC103379
0.8493	Intermediate Similarity	NPC477565
0.8435	Intermediate Similarity	NPC151895
0.8435	Intermediate Similarity	NPC88249
0.8435	Intermediate Similarity	NPC220858
0.8435	Intermediate Similarity	NPC192768
0.8435	Intermediate Similarity	NPC97221
0.8431	Intermediate Similarity	NPC4138
0.8431	Intermediate Similarity	NPC121275
0.8431	Intermediate Similarity	NPC284183
0.8356	Intermediate Similarity	NPC476151
0.8333	Intermediate Similarity	NPC54379
0.8333	Intermediate Similarity	NPC2413
0.8333	Intermediate Similarity	NPC276588
0.8333	Intermediate Similarity	NPC204828
0.8333	Intermediate Similarity	NPC39701
0.8333	Intermediate Similarity	NPC172765
0.8333	Intermediate Similarity	NPC207757
0.8333	Intermediate Similarity	NPC110416
0.8333	Intermediate Similarity	NPC295691
0.8333	Intermediate Similarity	NPC278799
0.8333	Intermediate Similarity	NPC193949
0.8333	Intermediate Similarity	NPC5238
0.8333	Intermediate Similarity	NPC127674
0.8333	Intermediate Similarity	NPC189266
0.8333	Intermediate Similarity	NPC249797
0.8333	Intermediate Similarity	NPC184026
0.8333	Intermediate Similarity	NPC469817
0.8321	Intermediate Similarity	NPC85276
0.828	Intermediate Similarity	NPC475215
0.828	Intermediate Similarity	NPC108434
0.8252	Intermediate Similarity	NPC314682
0.8239	Intermediate Similarity	NPC253429
0.8228	Intermediate Similarity	NPC192135
0.8228	Intermediate Similarity	NPC66341
0.8228	Intermediate Similarity	NPC477020
0.8217	Intermediate Similarity	NPC477562
0.8217	Intermediate Similarity	NPC26240
0.8217	Intermediate Similarity	NPC109925
0.8217	Intermediate Similarity	NPC69712
0.8194	Intermediate Similarity	NPC188163
0.8194	Intermediate Similarity	NPC213206
0.8194	Intermediate Similarity	NPC474915
0.8194	Intermediate Similarity	NPC328750
0.8151	Intermediate Similarity	NPC125852
0.8143	Intermediate Similarity	NPC149379
0.8117	Intermediate Similarity	NPC166014
0.8117	Intermediate Similarity	NPC27410
0.8079	Intermediate Similarity	NPC133011
0.8079	Intermediate Similarity	NPC82285
0.8052	Intermediate Similarity	NPC111485
0.8042	Intermediate Similarity	NPC131204
0.8042	Intermediate Similarity	NPC301050
0.8039	Intermediate Similarity	NPC203784
0.8039	Intermediate Similarity	NPC170503
0.8039	Intermediate Similarity	NPC126519
0.8039	Intermediate Similarity	NPC147091
0.8025	Intermediate Similarity	NPC474507
0.8013	Intermediate Similarity	NPC1229
0.8012	Intermediate Similarity	NPC148709
0.8012	Intermediate Similarity	NPC476577
0.8012	Intermediate Similarity	NPC173416
0.8	Intermediate Similarity	NPC146422
0.7987	Intermediate Similarity	NPC79328
0.7987	Intermediate Similarity	NPC152212
0.7974	Intermediate Similarity	NPC187022
0.7974	Intermediate Similarity	NPC80129
0.7962	Intermediate Similarity	NPC276944
0.7962	Intermediate Similarity	NPC232514
0.7962	Intermediate Similarity	NPC238530
0.7959	Intermediate Similarity	NPC136860
0.7959	Intermediate Similarity	NPC128019
0.7959	Intermediate Similarity	NPC476567
0.7958	Intermediate Similarity	NPC160692
0.7929	Intermediate Similarity	NPC271808
0.7911	Intermediate Similarity	NPC42549
0.7911	Intermediate Similarity	NPC240841
0.7911	Intermediate Similarity	NPC256012
0.7911	Intermediate Similarity	NPC317272
0.7911	Intermediate Similarity	NPC264850
0.7911	Intermediate Similarity	NPC250846
0.7911	Intermediate Similarity	NPC13916
0.7911	Intermediate Similarity	NPC268503
0.7898	Intermediate Similarity	NPC324144
0.7879	Intermediate Similarity	NPC135772
0.7867	Intermediate Similarity	NPC106295
0.7867	Intermediate Similarity	NPC51957
0.7867	Intermediate Similarity	NPC476144
0.7867	Intermediate Similarity	NPC210437
0.7867	Intermediate Similarity	NPC16107
0.7866	Intermediate Similarity	NPC477561
0.7866	Intermediate Similarity	NPC155442
0.7866	Intermediate Similarity	NPC476574
0.7866	Intermediate Similarity	NPC312918
0.7862	Intermediate Similarity	NPC145832
0.7862	Intermediate Similarity	NPC12053
0.7862	Intermediate Similarity	NPC81218
0.7862	Intermediate Similarity	NPC117188
0.7862	Intermediate Similarity	NPC205421
0.7862	Intermediate Similarity	NPC474931
0.7862	Intermediate Similarity	NPC158376
0.7862	Intermediate Similarity	NPC306555
0.7857	Intermediate Similarity	NPC8305
0.7857	Intermediate Similarity	NPC66177
0.7857	Intermediate Similarity	NPC268763
0.7848	Intermediate Similarity	NPC78222
0.7848	Intermediate Similarity	NPC477563
0.7848	Intermediate Similarity	NPC306843
0.7848	Intermediate Similarity	NPC96603
0.7848	Intermediate Similarity	NPC196447
0.7848	Intermediate Similarity	NPC24465
0.7848	Intermediate Similarity	NPC13504
0.7848	Intermediate Similarity	NPC212794
0.7848	Intermediate Similarity	NPC253043
0.7848	Intermediate Similarity	NPC136508
0.7843	Intermediate Similarity	NPC37272
0.784	Intermediate Similarity	NPC477558
0.7829	Intermediate Similarity	NPC274026
0.7815	Intermediate Similarity	NPC7467
0.7815	Intermediate Similarity	NPC475959
0.7812	Intermediate Similarity	NPC204908
0.7812	Intermediate Similarity	NPC83198
0.7806	Intermediate Similarity	NPC29647
0.7806	Intermediate Similarity	NPC186063
0.7801	Intermediate Similarity	NPC124802
0.7786	Intermediate Similarity	NPC236347
0.7786	Intermediate Similarity	NPC323775
0.7785	Intermediate Similarity	NPC475393
0.7771	Intermediate Similarity	NPC205167
0.7771	Intermediate Similarity	NPC249274
0.7762	Intermediate Similarity	NPC208757
0.775	Intermediate Similarity	NPC210140
0.7746	Intermediate Similarity	NPC126859
0.7746	Intermediate Similarity	NPC259665
0.7746	Intermediate Similarity	NPC89769
0.7736	Intermediate Similarity	NPC209377
0.7727	Intermediate Similarity	NPC26601
0.7722	Intermediate Similarity	NPC60186
0.7721	Intermediate Similarity	NPC268572
0.7704	Intermediate Similarity	NPC283468
0.7702	Intermediate Similarity	NPC477185
0.7702	Intermediate Similarity	NPC66573
0.7692	Intermediate Similarity	NPC274661
0.7692	Intermediate Similarity	NPC175890
0.7692	Intermediate Similarity	NPC48490
0.7692	Intermediate Similarity	NPC11296
0.7692	Intermediate Similarity	NPC82457
0.7692	Intermediate Similarity	NPC37205
0.7692	Intermediate Similarity	NPC160931
0.7688	Intermediate Similarity	NPC195392
0.7688	Intermediate Similarity	NPC86144
0.7688	Intermediate Similarity	NPC223077
0.7688	Intermediate Similarity	NPC193853
0.7688	Intermediate Similarity	NPC56887
0.7688	Intermediate Similarity	NPC304659
0.7673	Intermediate Similarity	NPC189470
0.7669	Intermediate Similarity	NPC477187
0.7669	Intermediate Similarity	NPC232386
0.7669	Intermediate Similarity	NPC152680
0.7669	Intermediate Similarity	NPC190783
0.7662	Intermediate Similarity	NPC326316
0.7662	Intermediate Similarity	NPC81733
0.7654	Intermediate Similarity	NPC118274
0.7654	Intermediate Similarity	NPC168753
0.7647	Intermediate Similarity	NPC191132
0.7647	Intermediate Similarity	NPC60295
0.7647	Intermediate Similarity	NPC122009
0.7643	Intermediate Similarity	NPC475326
0.764	Intermediate Similarity	NPC298979
0.7633	Intermediate Similarity	NPC186546
0.7633	Intermediate Similarity	NPC476576
0.7625	Intermediate Similarity	NPC134858
0.7622	Intermediate Similarity	NPC160193

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 NPC219233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	699
0.2-0.3	1089
0.3-0.4	1497
0.4-0.5	3128
0.5-0.6	1847
0.6-0.7	568
0.7-0.8	133
0.8-0.85	14
0.85-0.9	5
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9559	High Similarity	NPD3845	Phase 1
0.9416	High Similarity	NPD2422	Clinical (unspecified phase)
0.9259	High Similarity	NPD1632	Clinical (unspecified phase)
0.8931	High Similarity	NPD3055	Approved
0.8931	High Similarity	NPD3053	Approved
0.8881	High Similarity	NPD2028	Clinical (unspecified phase)
0.8712	High Similarity	NPD5311	Approved
0.8712	High Similarity	NPD5310	Approved
0.8671	High Similarity	NPD2421	Approved
0.8671	High Similarity	NPD2420	Approved
0.8489	Intermediate Similarity	NPD823	Approved
0.8489	Intermediate Similarity	NPD817	Approved
0.8214	Intermediate Similarity	NPD3062	Approved
0.8214	Intermediate Similarity	NPD3061	Approved
0.8214	Intermediate Similarity	NPD3059	Approved
0.8194	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1136	Approved
0.8143	Intermediate Similarity	NPD1130	Approved
0.8143	Intermediate Similarity	NPD1132	Approved
0.8099	Intermediate Similarity	NPD5314	Approved
0.8071	Intermediate Similarity	NPD601	Approved
0.8071	Intermediate Similarity	NPD597	Approved
0.8071	Intermediate Similarity	NPD598	Approved
0.8	Intermediate Similarity	NPD9379	Approved
0.8	Intermediate Similarity	NPD9377	Approved
0.8	Intermediate Similarity	NPD6030	Approved
0.8	Intermediate Similarity	NPD6031	Approved
0.7974	Intermediate Similarity	NPD7298	Approved
0.7899	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4584	Approved
0.7867	Intermediate Similarity	NPD3645	Discontinued
0.7857	Intermediate Similarity	NPD3635	Approved
0.7857	Intermediate Similarity	NPD3636	Approved
0.7857	Intermediate Similarity	NPD3637	Approved
0.7852	Intermediate Similarity	NPD4093	Discontinued
0.7829	Intermediate Similarity	NPD1969	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1972	Approved
0.7829	Intermediate Similarity	NPD1973	Approved
0.7823	Intermediate Similarity	NPD4257	Approved
0.7823	Intermediate Similarity	NPD4256	Phase 2
0.7801	Intermediate Similarity	NPD3594	Approved
0.7801	Intermediate Similarity	NPD3595	Approved
0.7799	Intermediate Similarity	NPD4010	Discontinued
0.7786	Intermediate Similarity	NPD9619	Approved
0.7786	Intermediate Similarity	NPD9620	Approved
0.7786	Intermediate Similarity	NPD9621	Approved
0.7746	Intermediate Similarity	NPD5155	Approved
0.7746	Intermediate Similarity	NPD5156	Approved
0.7737	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD9622	Approved
0.7676	Intermediate Similarity	NPD2606	Approved
0.7676	Intermediate Similarity	NPD2605	Approved
0.7662	Intermediate Similarity	NPD4017	Approved
0.766	Intermediate Similarity	NPD2194	Approved
0.766	Intermediate Similarity	NPD2195	Approved
0.7647	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2561	Approved
0.7626	Intermediate Similarity	NPD2562	Approved
0.7603	Intermediate Similarity	NPD2568	Approved
0.76	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2898	Approved
0.7576	Intermediate Similarity	NPD6297	Approved
0.7564	Intermediate Similarity	NPD4772	Phase 2
0.7564	Intermediate Similarity	NPD4773	Phase 2
0.7562	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5241	Discontinued
0.7536	Intermediate Similarity	NPD9381	Approved
0.7536	Intermediate Similarity	NPD9384	Approved
0.7533	Intermediate Similarity	NPD3638	Discontinued
0.7533	Intermediate Similarity	NPD3060	Approved
0.7518	Intermediate Similarity	NPD5303	Approved
0.7518	Intermediate Similarity	NPD5304	Approved
0.75	Intermediate Similarity	NPD1753	Discontinued
0.75	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9569	Approved
0.7468	Intermediate Similarity	NPD2977	Approved
0.7468	Intermediate Similarity	NPD2978	Approved
0.7465	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4103	Phase 2
0.7447	Intermediate Similarity	NPD4659	Approved
0.7432	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3641	Approved
0.7419	Intermediate Similarity	NPD3640	Phase 3
0.7419	Intermediate Similarity	NPD3639	Approved
0.7407	Intermediate Similarity	NPD2229	Approved
0.7407	Intermediate Similarity	NPD2228	Approved
0.7407	Intermediate Similarity	NPD2234	Approved
0.7403	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4726	Approved
0.74	Intermediate Similarity	NPD4725	Approved
0.74	Intermediate Similarity	NPD4721	Approved
0.7396	Intermediate Similarity	NPD8053	Approved
0.7396	Intermediate Similarity	NPD6851	Approved
0.7396	Intermediate Similarity	NPD6853	Approved
0.7396	Intermediate Similarity	NPD8054	Approved
0.7391	Intermediate Similarity	NPD316	Approved
0.7375	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1792	Phase 2
0.7368	Intermediate Similarity	NPD3022	Approved
0.7368	Intermediate Similarity	NPD3021	Approved
0.7358	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7831	Phase 2
0.7329	Intermediate Similarity	NPD7833	Phase 2
0.7319	Intermediate Similarity	NPD9613	Approved
0.7319	Intermediate Similarity	NPD9615	Approved
0.7319	Intermediate Similarity	NPD9616	Approved
0.7305	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4162	Approved
0.7301	Intermediate Similarity	NPD6107	Approved
0.7286	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1751	Approved
0.7279	Intermediate Similarity	NPD259	Phase 1
0.7279	Intermediate Similarity	NPD2674	Phase 3
0.7273	Intermediate Similarity	NPD27	Approved
0.7273	Intermediate Similarity	NPD2489	Approved
0.726	Intermediate Similarity	NPD9536	Phase 1
0.726	Intermediate Similarity	NPD9537	Phase 1
0.7256	Intermediate Similarity	NPD4166	Phase 2
0.7255	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9608	Approved
0.7252	Intermediate Similarity	NPD9610	Approved
0.7226	Intermediate Similarity	NPD1793	Approved
0.7226	Intermediate Similarity	NPD9618	Approved
0.7226	Intermediate Similarity	NPD9614	Approved
0.7226	Intermediate Similarity	NPD1791	Approved
0.7214	Intermediate Similarity	NPD1922	Discontinued
0.7211	Intermediate Similarity	NPD5718	Phase 2
0.7208	Intermediate Similarity	NPD8131	Suspended
0.7208	Intermediate Similarity	NPD5160	Discontinued
0.7194	Intermediate Similarity	NPD16	Approved
0.7194	Intermediate Similarity	NPD856	Approved
0.7194	Intermediate Similarity	NPD317	Approved
0.7194	Intermediate Similarity	NPD318	Approved
0.7181	Intermediate Similarity	NPD555	Phase 2
0.7179	Intermediate Similarity	NPD2874	Phase 2
0.7176	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD257	Approved
0.7172	Intermediate Similarity	NPD602	Approved
0.7172	Intermediate Similarity	NPD258	Approved
0.7172	Intermediate Similarity	NPD599	Approved
0.7162	Intermediate Similarity	NPD6405	Approved
0.7162	Intermediate Similarity	NPD6407	Approved
0.7161	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1444	Approved
0.7143	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1445	Approved
0.7134	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3124	Discontinued
0.7108	Intermediate Similarity	NPD2969	Approved
0.7108	Intermediate Similarity	NPD5137	Approved
0.7108	Intermediate Similarity	NPD2970	Approved
0.7101	Intermediate Similarity	NPD7479	Phase 2
0.7095	Intermediate Similarity	NPD3144	Approved
0.7095	Intermediate Similarity	NPD3145	Approved
0.7086	Intermediate Similarity	NPD3553	Approved
0.7086	Intermediate Similarity	NPD3554	Approved
0.7086	Intermediate Similarity	NPD3552	Approved
0.7086	Intermediate Similarity	NPD3555	Approved
0.7078	Intermediate Similarity	NPD2460	Phase 3
0.7078	Intermediate Similarity	NPD2458	Approved
0.7078	Intermediate Similarity	NPD2459	Approved
0.707	Intermediate Similarity	NPD1424	Approved
0.7055	Intermediate Similarity	NPD859	Approved
0.7055	Intermediate Similarity	NPD858	Approved
0.7055	Intermediate Similarity	NPD7451	Discontinued
0.7048	Intermediate Similarity	NPD3051	Approved
0.7048	Intermediate Similarity	NPD6071	Discontinued
0.7047	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4656	Approved
0.7045	Intermediate Similarity	NPD4658	Approved
0.7039	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3364	Phase 3
0.7024	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3054	Approved
0.702	Intermediate Similarity	NPD3052	Approved
0.702	Intermediate Similarity	NPD2986	Phase 2
0.702	Intermediate Similarity	NPD2989	Phase 2
0.7006	Intermediate Similarity	NPD4083	Discontinued
0.7006	Intermediate Similarity	NPD7598	Phase 2
0.7	Intermediate Similarity	NPD826	Approved
0.7	Intermediate Similarity	NPD825	Approved
0.7	Intermediate Similarity	NPD3455	Phase 2
0.6994	Remote Similarity	NPD2560	Approved
0.6994	Remote Similarity	NPD2563	Approved
0.6993	Remote Similarity	NPD9570	Approved
0.6987	Remote Similarity	NPD302	Approved
0.6986	Remote Similarity	NPD1134	Approved
0.6986	Remote Similarity	NPD1129	Approved
0.6986	Remote Similarity	NPD1135	Approved
0.6986	Remote Similarity	NPD1131	Approved
0.6986	Remote Similarity	NPD1133	Approved
0.6982	Remote Similarity	NPD8251	Approved
0.6982	Remote Similarity	NPD8099	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data