NPASS Compound

Structure

CID33256 OpenBabel06191715362D 23 27 0 0 1 0 0 0 0 0999 V2000 -2.5873 -2.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -4.0827 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 -2.5981 -1.5000 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 -5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -1.7321 -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 1 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 -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 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -3.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 3 1 0 0 0 0 2 8 1 0 0 0 0 3 18 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 7 22 1 0 0 0 0 9 10 1 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 1 0 0 0 12 13 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 9 1 6 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 8 1 1 0 0 0 15 18 1 0 0 0 0 16 23 1 6 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.11
Volume:	301.572
LogP:	1.637
LogD:	1.652
LogS:	-3.11
# Rotatable Bonds:	0
TPSA:	68.23
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	4.19
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.678
MDCK Permeability:	5.204410263104364e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	69.33336639404297%
Volume Distribution (VD):	2.38
Pgp-substrate:	36.26542282104492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.824
CYP1A2-substrate:	0.651
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.626
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.726
CYP3A4-inhibitor:	0.646
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	15.784
Half-life (T1/2):	0.414

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.174
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.058
Carcinogencity:	0.845
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC33256

Natural Product ID:	NPC33256
*Common Name:**	DGQPIOQRPAGNGB-DANNLKNASA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Hippeastrine
Standard InCHIKey:	DGQPIOQRPAGNGB-DANNLKNASA-N
Standard InCHI:	InChI=1S/C17H17NO5/c1-18-3-2-8-4-11(19)16-14(15(8)18)9-5-12-13(22-7-21-12)6-10(9)17(20)23-16/h4-6,11,14-16,19H,2-3,7H2,1H3/t11-,14-,15+,16+/m0/s1
SMILES:	CN1CCC2=C[C@@H]([C@@H]3[C@H]([C@H]12)c1cc2OCOc2cc1C(=O)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457606
PubChem CID:	441594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004122] Homolycorine-type amaryllidaceae alkaloids

*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
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26604	Aralia subcapitata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26641	Pteroxygonum giraldii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21398	Jasminum laurifolium f. nitidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13480	Stereocaulon dactylophyllum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8546	Corydalis chaerophylla	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO272	Pittosporum eugenioides	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26604	Aralia subcapitata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23091	Halocarpus bidwillii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4316	Ananas sativus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7031	Salvia keerlii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26154	Erythropodium caribaeorum	Species	Anthothelidae	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
ED50	11
IC50	3
Others	1

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	6.3	ug ml-1	PMID[460927]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	7.8	ug ml-1	PMID[460927]
NPT2049	Cell Line	HT	Homo sapiens	ED50	=	4.7	ug ml-1	PMID[460927]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[460927]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[460927]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	5.2	ug ml-1	PMID[460927]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[460927]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	7.3	ug ml-1	PMID[460927]
NPT168	Cell Line	P388	Mus musculus	ED50	=	4.0	ug ml-1	PMID[460927]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[460927]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	12700.0	nM	PMID[460928]
NPT1019	Organism	Trichomonas vaginalis	Trichomonas vaginalis	Activity	=	13.0	%	PMID[460929]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[460930]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[460930]

☑ 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 NPC33256 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	255
0.1-0.2	1117
0.2-0.3	3176
0.3-0.4	8536
0.4-0.5	10031
0.5-0.6	8263
0.6-0.7	10287
0.7-0.8	929
0.8-0.85	70
0.85-0.9	21
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC162694
0.9399	High Similarity	NPC80472
0.9326	High Similarity	NPC94499
0.9249	High Similarity	NPC35680
0.905	High Similarity	NPC141440
0.8994	High Similarity	NPC230098
0.8927	High Similarity	NPC474745
0.887	High Similarity	NPC474325
0.8824	High Similarity	NPC286135
0.8814	High Similarity	NPC237044
0.8778	High Similarity	NPC474746
0.8778	High Similarity	NPC475981
0.8757	High Similarity	NPC304675
0.8588	High Similarity	NPC474708
0.8531	High Similarity	NPC475845
0.8506	High Similarity	NPC4304
0.8475	Intermediate Similarity	NPC181653
0.8475	Intermediate Similarity	NPC474324
0.8475	Intermediate Similarity	NPC190332
0.8475	Intermediate Similarity	NPC57812
0.8371	Intermediate Similarity	NPC100566
0.8362	Intermediate Similarity	NPC35345
0.8342	Intermediate Similarity	NPC226708
0.8316	Intermediate Similarity	NPC124302
0.8316	Intermediate Similarity	NPC14622
0.8316	Intermediate Similarity	NPC46744
0.8316	Intermediate Similarity	NPC70290
0.8316	Intermediate Similarity	NPC73020
0.8316	Intermediate Similarity	NPC215098
0.8305	Intermediate Similarity	NPC320104
0.8297	Intermediate Similarity	NPC474470
0.8238	Intermediate Similarity	NPC328700
0.8238	Intermediate Similarity	NPC119818
0.8238	Intermediate Similarity	NPC2173
0.8238	Intermediate Similarity	NPC202771
0.8229	Intermediate Similarity	NPC226652
0.8229	Intermediate Similarity	NPC314100
0.8229	Intermediate Similarity	NPC72788
0.8229	Intermediate Similarity	NPC120671
0.8205	Intermediate Similarity	NPC476500
0.8167	Intermediate Similarity	NPC252960
0.8148	Intermediate Similarity	NPC319549
0.8138	Intermediate Similarity	NPC166979
0.8132	Intermediate Similarity	NPC470739
0.8132	Intermediate Similarity	NPC225597
0.8132	Intermediate Similarity	NPC477640
0.8111	Intermediate Similarity	NPC476002
0.8101	Intermediate Similarity	NPC218614
0.8083	Intermediate Similarity	NPC267414
0.8077	Intermediate Similarity	NPC474475
0.8053	Intermediate Similarity	NPC63152
0.8051	Intermediate Similarity	NPC67346
0.8022	Intermediate Similarity	NPC158148
0.8022	Intermediate Similarity	NPC475686
0.8022	Intermediate Similarity	NPC266176
0.8022	Intermediate Similarity	NPC58766
0.8022	Intermediate Similarity	NPC290759
0.8022	Intermediate Similarity	NPC82533
0.8022	Intermediate Similarity	NPC86469
0.8021	Intermediate Similarity	NPC125924
0.7989	Intermediate Similarity	NPC26353
0.7989	Intermediate Similarity	NPC249274
0.7989	Intermediate Similarity	NPC205167
0.7978	Intermediate Similarity	NPC311991
0.7969	Intermediate Similarity	NPC469816
0.7969	Intermediate Similarity	NPC469815
0.7968	Intermediate Similarity	NPC473562
0.7959	Intermediate Similarity	NPC43069
0.7959	Intermediate Similarity	NPC97086
0.7959	Intermediate Similarity	NPC140577
0.7956	Intermediate Similarity	NPC180306
0.7946	Intermediate Similarity	NPC308267
0.7946	Intermediate Similarity	NPC187678
0.7937	Intermediate Similarity	NPC18306
0.7914	Intermediate Similarity	NPC27887
0.7897	Intermediate Similarity	NPC207239
0.7889	Intermediate Similarity	NPC97072
0.7889	Intermediate Similarity	NPC215829
0.7887	Intermediate Similarity	NPC24228
0.7868	Intermediate Similarity	NPC243483
0.7868	Intermediate Similarity	NPC232533
0.7861	Intermediate Similarity	NPC294790
0.7861	Intermediate Similarity	NPC148693
0.7861	Intermediate Similarity	NPC15919
0.7861	Intermediate Similarity	NPC118633
0.7842	Intermediate Similarity	NPC214629
0.7838	Intermediate Similarity	NPC303581
0.7838	Intermediate Similarity	NPC227683
0.7838	Intermediate Similarity	NPC67978
0.7817	Intermediate Similarity	NPC311781
0.7789	Intermediate Similarity	NPC268077
0.7789	Intermediate Similarity	NPC475566
0.7784	Intermediate Similarity	NPC474953
0.7772	Intermediate Similarity	NPC100420
0.7766	Intermediate Similarity	NPC329816
0.7766	Intermediate Similarity	NPC474427
0.7753	Intermediate Similarity	NPC223124
0.775	Intermediate Similarity	NPC475768
0.7749	Intermediate Similarity	NPC9867
0.7744	Intermediate Similarity	NPC470646
0.7744	Intermediate Similarity	NPC477258
0.7739	Intermediate Similarity	NPC207971
0.7725	Intermediate Similarity	NPC244554
0.7725	Intermediate Similarity	NPC149285
0.7725	Intermediate Similarity	NPC32154
0.7725	Intermediate Similarity	NPC469438
0.7725	Intermediate Similarity	NPC99179
0.7723	Intermediate Similarity	NPC46990
0.7713	Intermediate Similarity	NPC241704
0.7711	Intermediate Similarity	NPC157958
0.7708	Intermediate Similarity	NPC169387
0.7708	Intermediate Similarity	NPC477259
0.7704	Intermediate Similarity	NPC475713
0.7704	Intermediate Similarity	NPC474432
0.7701	Intermediate Similarity	NPC329992
0.7701	Intermediate Similarity	NPC2314
0.7692	Intermediate Similarity	NPC165797
0.7684	Intermediate Similarity	NPC298339
0.768	Intermediate Similarity	NPC196231
0.7676	Intermediate Similarity	NPC301189
0.7676	Intermediate Similarity	NPC298186
0.7667	Intermediate Similarity	NPC78733
0.766	Intermediate Similarity	NPC49353
0.7654	Intermediate Similarity	NPC270811
0.7654	Intermediate Similarity	NPC471073
0.7653	Intermediate Similarity	NPC174783
0.765	Intermediate Similarity	NPC68619
0.7647	Intermediate Similarity	NPC65403
0.7647	Intermediate Similarity	NPC57272
0.7644	Intermediate Similarity	NPC102760
0.764	Intermediate Similarity	NPC223125
0.7638	Intermediate Similarity	NPC254045
0.7638	Intermediate Similarity	NPC151470
0.7638	Intermediate Similarity	NPC201055
0.7638	Intermediate Similarity	NPC64576
0.7614	Intermediate Similarity	NPC204580
0.7614	Intermediate Similarity	NPC66909
0.7609	Intermediate Similarity	NPC218471
0.7609	Intermediate Similarity	NPC474770
0.7609	Intermediate Similarity	NPC239818
0.7596	Intermediate Similarity	NPC316368
0.7596	Intermediate Similarity	NPC135006
0.7596	Intermediate Similarity	NPC284236
0.7596	Intermediate Similarity	NPC226759
0.7594	Intermediate Similarity	NPC75958
0.7592	Intermediate Similarity	NPC474607
0.7592	Intermediate Similarity	NPC115906
0.7586	Intermediate Similarity	NPC94687
0.7586	Intermediate Similarity	NPC106840
0.7586	Intermediate Similarity	NPC476495
0.7584	Intermediate Similarity	NPC469539
0.7584	Intermediate Similarity	NPC470088
0.7584	Intermediate Similarity	NPC469540
0.7579	Intermediate Similarity	NPC121400
0.7576	Intermediate Similarity	NPC71124
0.7576	Intermediate Similarity	NPC83019
0.7574	Intermediate Similarity	NPC126211
0.7568	Intermediate Similarity	NPC231198
0.7568	Intermediate Similarity	NPC247972
0.7565	Intermediate Similarity	NPC188217
0.7552	Intermediate Similarity	NPC248642
0.7552	Intermediate Similarity	NPC275132
0.7552	Intermediate Similarity	NPC474650
0.7549	Intermediate Similarity	NPC476496
0.7548	Intermediate Similarity	NPC328856
0.7548	Intermediate Similarity	NPC478046
0.7548	Intermediate Similarity	NPC478047
0.7548	Intermediate Similarity	NPC321226
0.7548	Intermediate Similarity	NPC314914
0.7548	Intermediate Similarity	NPC180210
0.7541	Intermediate Similarity	NPC59028
0.7541	Intermediate Similarity	NPC69360
0.7541	Intermediate Similarity	NPC92191
0.754	Intermediate Similarity	NPC180586
0.7538	Intermediate Similarity	NPC470642
0.7537	Intermediate Similarity	NPC326895
0.7528	Intermediate Similarity	NPC214239
0.7527	Intermediate Similarity	NPC474858
0.7527	Intermediate Similarity	NPC41009
0.7527	Intermediate Similarity	NPC147091
0.7514	Intermediate Similarity	NPC134905
0.7514	Intermediate Similarity	NPC36130
0.7514	Intermediate Similarity	NPC59567
0.7513	Intermediate Similarity	NPC156576
0.75	Intermediate Similarity	NPC478048
0.7488	Intermediate Similarity	NPC315253
0.7488	Intermediate Similarity	NPC128476
0.7487	Intermediate Similarity	NPC120012
0.7487	Intermediate Similarity	NPC114364
0.7487	Intermediate Similarity	NPC475865
0.7487	Intermediate Similarity	NPC320223
0.7487	Intermediate Similarity	NPC316539
0.7486	Intermediate Similarity	NPC10205
0.7474	Intermediate Similarity	NPC229166
0.7474	Intermediate Similarity	NPC199465
0.7474	Intermediate Similarity	NPC128560
0.7473	Intermediate Similarity	NPC308555
0.7473	Intermediate Similarity	NPC137813
0.7461	Intermediate Similarity	NPC116284
0.7459	Intermediate Similarity	NPC153631

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 NPC33256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	556
0.2-0.3	1247
0.3-0.4	2255
0.4-0.5	2481
0.5-0.6	1658
0.6-0.7	662
0.7-0.8	104
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8316	Intermediate Similarity	NPD4420	Approved
0.8238	Intermediate Similarity	NPD5006	Approved
0.8238	Intermediate Similarity	NPD5005	Approved
0.8148	Intermediate Similarity	NPD7296	Approved
0.8098	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD3057	Approved
0.7959	Intermediate Similarity	NPD2972	Approved
0.7959	Intermediate Similarity	NPD3533	Approved
0.7949	Intermediate Similarity	NPD4107	Approved
0.7926	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6386	Approved
0.791	Intermediate Similarity	NPD6385	Approved
0.7868	Intermediate Similarity	NPD3448	Approved
0.7868	Intermediate Similarity	NPD2491	Approved
0.7817	Intermediate Similarity	NPD4482	Phase 3
0.7734	Intermediate Similarity	NPD5676	Approved
0.772	Intermediate Similarity	NPD2490	Approved
0.772	Intermediate Similarity	NPD2488	Approved
0.7716	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4665	Approved
0.7644	Intermediate Similarity	NPD4111	Phase 1
0.7638	Intermediate Similarity	NPD3450	Approved
0.7638	Intermediate Similarity	NPD2494	Approved
0.7638	Intermediate Similarity	NPD3452	Approved
0.7638	Intermediate Similarity	NPD2493	Approved
0.7614	Intermediate Similarity	NPD2975	Approved
0.7614	Intermediate Similarity	NPD2973	Approved
0.7614	Intermediate Similarity	NPD2974	Approved
0.7612	Intermediate Similarity	NPD4582	Approved
0.7612	Intermediate Similarity	NPD4583	Approved
0.7592	Intermediate Similarity	NPD7280	Phase 3
0.7592	Intermediate Similarity	NPD2968	Approved
0.7592	Intermediate Similarity	NPD7281	Phase 3
0.7592	Intermediate Similarity	NPD2971	Approved
0.7588	Intermediate Similarity	NPD4580	Approved
0.7581	Intermediate Similarity	NPD2970	Approved
0.7581	Intermediate Similarity	NPD2969	Approved
0.7571	Intermediate Similarity	NPD7907	Approved
0.7562	Intermediate Similarity	NPD4002	Approved
0.7562	Intermediate Similarity	NPD4004	Approved
0.7562	Intermediate Similarity	NPD7497	Discontinued
0.754	Intermediate Similarity	NPD4481	Phase 3
0.7524	Intermediate Similarity	NPD7827	Phase 1
0.7513	Intermediate Similarity	NPD5312	Approved
0.7513	Intermediate Similarity	NPD5313	Approved
0.7488	Intermediate Similarity	NPD7999	Approved
0.7487	Intermediate Similarity	NPD7038	Approved
0.7487	Intermediate Similarity	NPD7039	Approved
0.7486	Intermediate Similarity	NPD5353	Approved
0.7465	Intermediate Similarity	NPD6625	Approved
0.7449	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD27	Approved
0.7447	Intermediate Similarity	NPD2489	Approved
0.7446	Intermediate Similarity	NPD4966	Approved
0.7446	Intermediate Similarity	NPD4965	Approved
0.7446	Intermediate Similarity	NPD4967	Phase 2
0.7433	Intermediate Similarity	NPD3051	Approved
0.7394	Intermediate Similarity	NPD5242	Approved
0.7391	Intermediate Similarity	NPD5978	Approved
0.7391	Intermediate Similarity	NPD5977	Approved
0.7387	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5980	Discovery
0.7371	Intermediate Similarity	NPD6997	Phase 2
0.7368	Intermediate Similarity	NPD7930	Approved
0.7366	Intermediate Similarity	NPD6234	Discontinued
0.736	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7047	Phase 3
0.7318	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3640	Phase 3
0.7293	Intermediate Similarity	NPD3641	Approved
0.7293	Intermediate Similarity	NPD3639	Approved
0.7287	Intermediate Similarity	NPD6107	Approved
0.7285	Intermediate Similarity	NPD7048	Phase 3
0.7283	Intermediate Similarity	NPD37	Approved
0.7277	Intermediate Similarity	NPD7228	Approved
0.7268	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4040	Phase 1
0.7255	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD2977	Approved
0.7243	Intermediate Similarity	NPD2978	Approved
0.7231	Intermediate Similarity	NPD7313	Approved
0.7231	Intermediate Similarity	NPD7312	Approved
0.7231	Intermediate Similarity	NPD7311	Approved
0.7231	Intermediate Similarity	NPD7310	Approved
0.7228	Intermediate Similarity	NPD4773	Phase 2
0.7228	Intermediate Similarity	NPD4772	Phase 2
0.7217	Intermediate Similarity	NPD8404	Phase 2
0.7213	Intermediate Similarity	NPD824	Approved
0.7207	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7309	Approved
0.7192	Intermediate Similarity	NPD7565	Approved
0.7173	Intermediate Similarity	NPD2898	Approved
0.7163	Intermediate Similarity	NPD7701	Phase 2
0.7157	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5772	Approved
0.7151	Intermediate Similarity	NPD5773	Approved
0.715	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6873	Phase 2
0.7128	Intermediate Similarity	NPD7685	Pre-registration
0.7121	Intermediate Similarity	NPD4663	Approved
0.7112	Intermediate Similarity	NPD2563	Approved
0.7112	Intermediate Similarity	NPD2560	Approved
0.7104	Intermediate Similarity	NPD1670	Discontinued
0.7101	Intermediate Similarity	NPD8319	Approved
0.7101	Intermediate Similarity	NPD8320	Phase 1
0.7098	Intermediate Similarity	NPD7177	Discontinued
0.7095	Intermediate Similarity	NPD4236	Phase 3
0.7095	Intermediate Similarity	NPD4237	Approved
0.7085	Intermediate Similarity	NPD7906	Approved
0.7083	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4859	Phase 1
0.7068	Intermediate Similarity	NPD5711	Approved
0.7068	Intermediate Similarity	NPD6071	Discontinued
0.7068	Intermediate Similarity	NPD5710	Approved
0.7065	Intermediate Similarity	NPD4210	Discontinued
0.7056	Intermediate Similarity	NPD4577	Approved
0.7056	Intermediate Similarity	NPD4578	Approved
0.705	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7240	Approved
0.7027	Intermediate Similarity	NPD3455	Phase 2
0.7027	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6853	Approved
0.702	Intermediate Similarity	NPD6851	Approved
0.7017	Intermediate Similarity	NPD5241	Discontinued
0.7016	Intermediate Similarity	NPD7199	Phase 2
0.701	Intermediate Similarity	NPD5564	Approved
0.701	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6723	Discontinued
0.6995	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6778	Approved
0.699	Remote Similarity	NPD6776	Approved
0.699	Remote Similarity	NPD6782	Approved
0.699	Remote Similarity	NPD6297	Approved
0.699	Remote Similarity	NPD6780	Approved
0.699	Remote Similarity	NPD6779	Approved
0.699	Remote Similarity	NPD6777	Approved
0.699	Remote Similarity	NPD3823	Discontinued
0.699	Remote Similarity	NPD6781	Approved
0.6981	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7783	Phase 2
0.6979	Remote Similarity	NPD7315	Approved
0.6974	Remote Similarity	NPD5844	Phase 1
0.6973	Remote Similarity	NPD3686	Approved
0.6973	Remote Similarity	NPD3687	Approved
0.6967	Remote Similarity	NPD8151	Discontinued
0.6961	Remote Similarity	NPD5582	Discontinued
0.6952	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7110	Phase 1
0.695	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7874	Approved
0.6934	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2163	Approved
0.6919	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6842	Approved
0.6915	Remote Similarity	NPD6841	Approved
0.6915	Remote Similarity	NPD7291	Discontinued
0.6915	Remote Similarity	NPD6843	Phase 3
0.6898	Remote Similarity	NPD6876	Approved
0.6898	Remote Similarity	NPD6875	Approved
0.6895	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6666	Approved
0.6885	Remote Similarity	NPD6667	Approved
0.6885	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4361	Phase 2
0.6872	Remote Similarity	NPD7583	Approved
0.6868	Remote Similarity	NPD4628	Phase 3
0.686	Remote Similarity	NPD7810	Phase 3
0.686	Remote Similarity	NPD7811	Phase 3
0.6856	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8469	Approved
0.6847	Remote Similarity	NPD8059	Phase 3
0.6842	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7585	Approved
0.6834	Remote Similarity	NPD7549	Discontinued
0.6828	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7577	Discontinued
0.6822	Remote Similarity	NPD683	Approved
0.6822	Remote Similarity	NPD7801	Approved
0.6821	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2569	Approved
0.6816	Remote Similarity	NPD2567	Approved
0.6816	Remote Similarity	NPD5036	Approved
0.6811	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD4584	Approved
0.681	Remote Similarity	NPD7696	Phase 3
0.681	Remote Similarity	NPD7698	Approved
0.681	Remote Similarity	NPD7697	Approved
0.681	Remote Similarity	NPD7435	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