NPASS Compound

Structure

CID165797 OpenBabel06191715532D 23 27 0 0 1 0 0 0 0 0999 V2000 3.2303 2.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1695 1.1182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4088 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2889 1.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9909 0.1342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0790 1.7594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4615 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5789 2.5125 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9227 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9227 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4985 2.1195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 0.9010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.3564 3.4874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3569 2.6324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8738 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8738 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 11 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 19 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.15
Volume:	312.714
LogP:	2.361
LogD:	2.415
LogS:	-3.384
# Rotatable Bonds:	1
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.858
Synthetic Accessibility Score:	4.322
Fsp3:	0.556
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:	-4.677
MDCK Permeability:	2.1349380403989926e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.369
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995
Plasma Protein Binding (PPB):	50.60260772705078%
Volume Distribution (VD):	2.427
Pgp-substrate:	48.64295196533203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.907
CYP1A2-substrate:	0.736
CYP2C19-inhibitor:	0.301
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	0.329
CYP2D6-inhibitor:	0.922
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.864
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	13.885
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.779
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.458
Rat Oral Acute Toxicity:	0.413
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.108
Carcinogencity:	0.86
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC165797

Natural Product ID:	NPC165797
*Common Name:**	Isocephalotaxine
IUPAC Name:	n.a.
Synonyms:	Isocephalotaxine
Standard InCHIKey:	PQWZXENVZQJUKV-UWBLVGDVSA-N
Standard InCHI:	InChI=1S/C18H21NO4/c1-21-17-13(20)9-18-4-2-5-19(18)6-3-11-7-14-15(23-10-22-14)8-12(11)16(17)18/h7-8,13,20H,2-6,9-10H2,1H3/t13?,18-/m0/s1
SMILES:	COC1=C2c3cc4c(cc3CCN3CCC[C@]23CC1O)OCO4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517319
PubChem CID:	10245167
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003778] Cephalotaxus 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
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	15.0	ug.mL-1	PMID[547747]

☑ 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 NPC165797 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	232
0.1-0.2	1243
0.2-0.3	4889
0.3-0.4	13117
0.4-0.5	7899
0.5-0.6	11345
0.6-0.7	3131
0.7-0.8	725
0.8-0.85	78
0.85-0.9	31
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9057	High Similarity	NPC301189
0.9057	High Similarity	NPC298186
0.8994	High Similarity	NPC476002
0.8889	High Similarity	NPC57272
0.8589	High Similarity	NPC100566
0.8509	High Similarity	NPC215829
0.8509	High Similarity	NPC97072
0.8476	Intermediate Similarity	NPC190332
0.8476	Intermediate Similarity	NPC181653
0.8333	Intermediate Similarity	NPC319549
0.8323	Intermediate Similarity	NPC477640
0.8323	Intermediate Similarity	NPC225597
0.8323	Intermediate Similarity	NPC470739
0.8313	Intermediate Similarity	NPC290759
0.8313	Intermediate Similarity	NPC82533
0.8313	Intermediate Similarity	NPC158148
0.8313	Intermediate Similarity	NPC266176
0.8313	Intermediate Similarity	NPC58766
0.8313	Intermediate Similarity	NPC475686
0.8293	Intermediate Similarity	NPC320104
0.8284	Intermediate Similarity	NPC237044
0.8282	Intermediate Similarity	NPC4304
0.8263	Intermediate Similarity	NPC311991
0.8263	Intermediate Similarity	NPC474475
0.8261	Intermediate Similarity	NPC78733
0.8253	Intermediate Similarity	NPC252960
0.825	Intermediate Similarity	NPC148898
0.8235	Intermediate Similarity	NPC474325
0.8225	Intermediate Similarity	NPC304675
0.8187	Intermediate Similarity	NPC474745
0.8182	Intermediate Similarity	NPC218614
0.8125	Intermediate Similarity	NPC274026
0.8118	Intermediate Similarity	NPC187678
0.811	Intermediate Similarity	NPC111485
0.8098	Intermediate Similarity	NPC147091
0.807	Intermediate Similarity	NPC474470
0.8061	Intermediate Similarity	NPC205167
0.8046	Intermediate Similarity	NPC474746
0.8046	Intermediate Similarity	NPC475981
0.8025	Intermediate Similarity	NPC82285
0.8025	Intermediate Similarity	NPC233029
0.8025	Intermediate Similarity	NPC223124
0.8025	Intermediate Similarity	NPC210148
0.8025	Intermediate Similarity	NPC133011
0.8024	Intermediate Similarity	NPC276944
0.8024	Intermediate Similarity	NPC232514
0.8024	Intermediate Similarity	NPC238530
0.8023	Intermediate Similarity	NPC15919
0.8	Intermediate Similarity	NPC475959
0.7977	Intermediate Similarity	NPC244554
0.7955	Intermediate Similarity	NPC230098
0.7953	Intermediate Similarity	NPC2314
0.7952	Intermediate Similarity	NPC249274
0.7929	Intermediate Similarity	NPC474324
0.7929	Intermediate Similarity	NPC57812
0.7919	Intermediate Similarity	NPC118633
0.7919	Intermediate Similarity	NPC148693
0.7919	Intermediate Similarity	NPC294790
0.7917	Intermediate Similarity	NPC231198
0.7907	Intermediate Similarity	NPC49353
0.7901	Intermediate Similarity	NPC223125
0.7892	Intermediate Similarity	NPC92191
0.7892	Intermediate Similarity	NPC59028
0.7882	Intermediate Similarity	NPC475845
0.7879	Intermediate Similarity	NPC31311
0.7879	Intermediate Similarity	NPC234392
0.7874	Intermediate Similarity	NPC99179
0.7871	Intermediate Similarity	NPC7018
0.7844	Intermediate Similarity	NPC18402
0.7836	Intermediate Similarity	NPC474708
0.7836	Intermediate Similarity	NPC75958
0.7831	Intermediate Similarity	NPC78359
0.7831	Intermediate Similarity	NPC148014
0.7831	Intermediate Similarity	NPC315707
0.7831	Intermediate Similarity	NPC65490
0.7831	Intermediate Similarity	NPC40389
0.7818	Intermediate Similarity	NPC41178
0.7818	Intermediate Similarity	NPC138487
0.7818	Intermediate Similarity	NPC216459
0.7812	Intermediate Similarity	NPC130926
0.7797	Intermediate Similarity	NPC9867
0.7791	Intermediate Similarity	NPC65403
0.7784	Intermediate Similarity	NPC477080
0.7778	Intermediate Similarity	NPC428
0.7778	Intermediate Similarity	NPC476571
0.7778	Intermediate Similarity	NPC24233
0.7778	Intermediate Similarity	NPC135538
0.7778	Intermediate Similarity	NPC147390
0.7778	Intermediate Similarity	NPC246587
0.7771	Intermediate Similarity	NPC146288
0.7759	Intermediate Similarity	NPC283999
0.7725	Intermediate Similarity	NPC475326
0.7725	Intermediate Similarity	NPC129603
0.7716	Intermediate Similarity	NPC191376
0.7716	Intermediate Similarity	NPC179825
0.7716	Intermediate Similarity	NPC321505
0.7706	Intermediate Similarity	NPC247972
0.7706	Intermediate Similarity	NPC180306
0.7702	Intermediate Similarity	NPC185838
0.7692	Intermediate Similarity	NPC33256
0.7683	Intermediate Similarity	NPC220858
0.7683	Intermediate Similarity	NPC151895
0.7683	Intermediate Similarity	NPC97221
0.7683	Intermediate Similarity	NPC88249
0.7683	Intermediate Similarity	NPC192768
0.7679	Intermediate Similarity	NPC69360
0.7665	Intermediate Similarity	NPC160931
0.7665	Intermediate Similarity	NPC37205
0.7647	Intermediate Similarity	NPC59567
0.7647	Intermediate Similarity	NPC233650
0.7643	Intermediate Similarity	NPC131204
0.7643	Intermediate Similarity	NPC301050
0.7622	Intermediate Similarity	NPC103379
0.7622	Intermediate Similarity	NPC477565
0.7616	Intermediate Similarity	NPC298979
0.7616	Intermediate Similarity	NPC210140
0.7607	Intermediate Similarity	NPC476151
0.7605	Intermediate Similarity	NPC207757
0.7605	Intermediate Similarity	NPC278799
0.7605	Intermediate Similarity	NPC193949
0.7605	Intermediate Similarity	NPC93593
0.7605	Intermediate Similarity	NPC276588
0.7605	Intermediate Similarity	NPC54379
0.7605	Intermediate Similarity	NPC295691
0.7605	Intermediate Similarity	NPC189266
0.7605	Intermediate Similarity	NPC184026
0.7605	Intermediate Similarity	NPC127674
0.7605	Intermediate Similarity	NPC5238
0.7605	Intermediate Similarity	NPC2413
0.7605	Intermediate Similarity	NPC204828
0.7605	Intermediate Similarity	NPC469817
0.7605	Intermediate Similarity	NPC110416
0.7605	Intermediate Similarity	NPC172765
0.7605	Intermediate Similarity	NPC39701
0.7605	Intermediate Similarity	NPC249797
0.7602	Intermediate Similarity	NPC134858
0.76	Intermediate Similarity	NPC199465
0.76	Intermediate Similarity	NPC229166
0.76	Intermediate Similarity	NPC128560
0.7595	Intermediate Similarity	NPC193528
0.759	Intermediate Similarity	NPC270811
0.759	Intermediate Similarity	NPC471073
0.7584	Intermediate Similarity	NPC275132
0.7584	Intermediate Similarity	NPC248642
0.758	Intermediate Similarity	NPC11147
0.7571	Intermediate Similarity	NPC126284
0.7562	Intermediate Similarity	NPC213206
0.7562	Intermediate Similarity	NPC328750
0.7562	Intermediate Similarity	NPC188163
0.7562	Intermediate Similarity	NPC474915
0.7544	Intermediate Similarity	NPC124433
0.7544	Intermediate Similarity	NPC293871
0.7542	Intermediate Similarity	NPC156576
0.7514	Intermediate Similarity	NPC114364
0.7514	Intermediate Similarity	NPC320223
0.7514	Intermediate Similarity	NPC150879
0.7514	Intermediate Similarity	NPC210918
0.75	Intermediate Similarity	NPC314682
0.75	Intermediate Similarity	NPC76079
0.7486	Intermediate Similarity	NPC102760
0.7486	Intermediate Similarity	NPC476331
0.7485	Intermediate Similarity	NPC145304
0.7484	Intermediate Similarity	NPC248505
0.7484	Intermediate Similarity	NPC95366
0.7484	Intermediate Similarity	NPC160193
0.7471	Intermediate Similarity	NPC106786
0.7469	Intermediate Similarity	NPC476567
0.7469	Intermediate Similarity	NPC136860
0.7469	Intermediate Similarity	NPC128019
0.7457	Intermediate Similarity	NPC124657
0.7456	Intermediate Similarity	NPC186063
0.7455	Intermediate Similarity	NPC37144
0.7455	Intermediate Similarity	NPC59907
0.7429	Intermediate Similarity	NPC474953
0.7427	Intermediate Similarity	NPC306902
0.7427	Intermediate Similarity	NPC477559
0.7427	Intermediate Similarity	NPC266753
0.7427	Intermediate Similarity	NPC232924
0.7427	Intermediate Similarity	NPC160298
0.7425	Intermediate Similarity	NPC277669
0.7425	Intermediate Similarity	NPC76213
0.7423	Intermediate Similarity	NPC294249
0.7421	Intermediate Similarity	NPC137172
0.7421	Intermediate Similarity	NPC145446
0.741	Intermediate Similarity	NPC207824
0.741	Intermediate Similarity	NPC60538
0.741	Intermediate Similarity	NPC211296
0.7399	Intermediate Similarity	NPC302527
0.7399	Intermediate Similarity	NPC89199
0.7399	Intermediate Similarity	NPC167546
0.7399	Intermediate Similarity	NPC54125
0.7399	Intermediate Similarity	NPC76116
0.7399	Intermediate Similarity	NPC16805
0.7394	Intermediate Similarity	NPC16107
0.7394	Intermediate Similarity	NPC210437
0.7394	Intermediate Similarity	NPC476144
0.7394	Intermediate Similarity	NPC106295
0.7394	Intermediate Similarity	NPC51957
0.7391	Intermediate Similarity	NPC94499
0.7389	Intermediate Similarity	NPC116284

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 NPC165797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	627
0.2-0.3	1189
0.3-0.4	2474
0.4-0.5	2587
0.5-0.6	1449
0.6-0.7	580
0.7-0.8	91
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7296	Approved
0.7862	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD2563	Approved
0.7831	Intermediate Similarity	NPD2560	Approved
0.7829	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2978	Approved
0.7771	Intermediate Similarity	NPD2977	Approved
0.775	Intermediate Similarity	NPD5241	Discontinued
0.7651	Intermediate Similarity	NPD4773	Phase 2
0.7651	Intermediate Similarity	NPD4772	Phase 2
0.7562	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6071	Discontinued
0.7516	Intermediate Similarity	NPD4237	Approved
0.7516	Intermediate Similarity	NPD4236	Phase 3
0.75	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7281	Phase 3
0.743	Intermediate Similarity	NPD7280	Phase 3
0.7414	Intermediate Similarity	NPD2969	Approved
0.7414	Intermediate Similarity	NPD2970	Approved
0.7394	Intermediate Similarity	NPD4584	Approved
0.7371	Intermediate Similarity	NPD2489	Approved
0.7371	Intermediate Similarity	NPD27	Approved
0.7365	Intermediate Similarity	NPD4210	Discontinued
0.7356	Intermediate Similarity	NPD3051	Approved
0.7353	Intermediate Similarity	NPD5773	Approved
0.7353	Intermediate Similarity	NPD5772	Approved
0.7301	Intermediate Similarity	NPD4162	Approved
0.7301	Intermediate Similarity	NPD3060	Approved
0.7273	Intermediate Similarity	NPD2898	Approved
0.7225	Intermediate Similarity	NPD7831	Phase 2
0.7225	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7833	Phase 2
0.7222	Intermediate Similarity	NPD2161	Phase 2
0.7198	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2674	Phase 3
0.7159	Intermediate Similarity	NPD4010	Discontinued
0.7134	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2238	Phase 2
0.7105	Intermediate Similarity	NPD1357	Approved
0.7102	Intermediate Similarity	NPD6107	Approved
0.7101	Intermediate Similarity	NPD3639	Approved
0.7101	Intermediate Similarity	NPD3641	Approved
0.7101	Intermediate Similarity	NPD3640	Phase 3
0.7099	Intermediate Similarity	NPD6895	Approved
0.7099	Intermediate Similarity	NPD6896	Approved
0.7091	Intermediate Similarity	NPD5177	Phase 3
0.7081	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3705	Approved
0.7073	Intermediate Similarity	NPD1375	Discontinued
0.7052	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2492	Phase 1
0.7037	Intermediate Similarity	NPD5582	Discontinued
0.7018	Intermediate Similarity	NPD4017	Approved
0.7	Intermediate Similarity	NPD6030	Approved
0.7	Intermediate Similarity	NPD5718	Phase 2
0.7	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3145	Approved
0.7	Intermediate Similarity	NPD3144	Approved
0.7	Intermediate Similarity	NPD6031	Approved
0.6994	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7298	Approved
0.6989	Remote Similarity	NPD7906	Approved
0.6983	Remote Similarity	NPD4481	Phase 3
0.6977	Remote Similarity	NPD6875	Approved
0.6977	Remote Similarity	NPD6876	Approved
0.6959	Remote Similarity	NPD3687	Approved
0.6959	Remote Similarity	NPD3686	Approved
0.6957	Remote Similarity	NPD7310	Approved
0.6957	Remote Similarity	NPD7311	Approved
0.6957	Remote Similarity	NPD7312	Approved
0.6957	Remote Similarity	NPD7313	Approved
0.6951	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2667	Approved
0.6948	Remote Similarity	NPD2668	Approved
0.6941	Remote Similarity	NPD7526	Approved
0.6941	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD52	Approved
0.6935	Remote Similarity	NPD4663	Approved
0.6923	Remote Similarity	NPD2233	Approved
0.6923	Remote Similarity	NPD2232	Approved
0.6923	Remote Similarity	NPD2230	Approved
0.6919	Remote Similarity	NPD7309	Approved
0.6919	Remote Similarity	NPD4005	Discontinued
0.6915	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2677	Approved
0.6894	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4739	Approved
0.6875	Remote Similarity	NPD4420	Approved
0.6872	Remote Similarity	NPD4166	Phase 2
0.6868	Remote Similarity	NPD5313	Approved
0.6868	Remote Similarity	NPD5312	Approved
0.6865	Remote Similarity	NPD4578	Approved
0.6865	Remote Similarity	NPD4577	Approved
0.6845	Remote Similarity	NPD6331	Phase 2
0.6845	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7110	Phase 1
0.6839	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8053	Approved
0.6828	Remote Similarity	NPD8054	Approved
0.6821	Remote Similarity	NPD5006	Approved
0.6821	Remote Similarity	NPD5005	Approved
0.681	Remote Similarity	NPD3620	Phase 2
0.681	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3692	Discontinued
0.678	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7124	Phase 2
0.676	Remote Similarity	NPD3365	Discontinued
0.6753	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1136	Approved
0.6748	Remote Similarity	NPD1132	Approved
0.6748	Remote Similarity	NPD1130	Approved
0.6747	Remote Similarity	NPD1753	Discontinued
0.6747	Remote Similarity	NPD4108	Discontinued
0.6744	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5604	Discontinued
0.6742	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD2488	Approved
0.6737	Remote Similarity	NPD2490	Approved
0.6727	Remote Similarity	NPD2653	Approved
0.6727	Remote Similarity	NPD2157	Approved
0.6726	Remote Similarity	NPD7153	Discontinued
0.6726	Remote Similarity	NPD7037	Approved
0.672	Remote Similarity	NPD6842	Approved
0.672	Remote Similarity	NPD6841	Approved
0.672	Remote Similarity	NPD6843	Phase 3
0.6705	Remote Similarity	NPD4727	Phase 1
0.6704	Remote Similarity	NPD6315	Phase 2
0.6703	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6297	Approved
0.6687	Remote Similarity	NPD598	Approved
0.6687	Remote Similarity	NPD597	Approved
0.6687	Remote Similarity	NPD601	Approved
0.6687	Remote Similarity	NPD6111	Discontinued
0.6686	Remote Similarity	NPD3158	Phase 1
0.6686	Remote Similarity	NPD3157	Approved
0.6686	Remote Similarity	NPD4123	Phase 3
0.6686	Remote Similarity	NPD7020	Approved
0.6686	Remote Similarity	NPD3645	Discontinued
0.6686	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7019	Approved
0.6685	Remote Similarity	NPD8156	Discontinued
0.6684	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7827	Phase 1
0.6667	Remote Similarity	NPD4666	Phase 3
0.6667	Remote Similarity	NPD4585	Approved
0.6667	Remote Similarity	NPD1793	Approved
0.6667	Remote Similarity	NPD3685	Discontinued
0.6667	Remote Similarity	NPD1791	Approved
0.6649	Remote Similarity	NPD6853	Approved
0.6649	Remote Similarity	NPD6851	Approved
0.6648	Remote Similarity	NPD5090	Approved
0.6648	Remote Similarity	NPD5089	Approved
0.6648	Remote Similarity	NPD4055	Discovery
0.6647	Remote Similarity	NPD5754	Discontinued
0.6647	Remote Similarity	NPD6090	Discontinued
0.6647	Remote Similarity	NPD2155	Approved
0.6647	Remote Similarity	NPD2154	Approved
0.6647	Remote Similarity	NPD2156	Approved
0.6646	Remote Similarity	NPD3163	Approved
0.6646	Remote Similarity	NPD3162	Approved
0.6632	Remote Similarity	NPD3349	Phase 2
0.663	Remote Similarity	NPD8099	Discontinued
0.663	Remote Similarity	NPD8251	Approved
0.663	Remote Similarity	NPD8252	Approved
0.6629	Remote Similarity	NPD824	Approved
0.6627	Remote Similarity	NPD823	Approved
0.6627	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD817	Approved
0.6613	Remote Similarity	NPD7007	Discovery
0.6611	Remote Similarity	NPD5709	Phase 3
0.6606	Remote Similarity	NPD3059	Approved
0.6606	Remote Similarity	NPD3062	Approved
0.6606	Remote Similarity	NPD3061	Approved
0.6596	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD4967	Phase 2
0.6592	Remote Similarity	NPD4965	Approved
0.6592	Remote Similarity	NPD4966	Approved
0.6584	Remote Similarity	NPD3055	Approved
0.6584	Remote Similarity	NPD3053	Approved
0.6584	Remote Similarity	NPD1817	Approved
0.6584	Remote Similarity	NPD1820	Approved
0.6584	Remote Similarity	NPD1818	Approved
0.6584	Remote Similarity	NPD1819	Approved
0.6579	Remote Similarity	NPD228	Approved
0.6576	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2120	Phase 2
0.657	Remote Similarity	NPD6667	Approved
0.657	Remote Similarity	NPD6666	Approved
0.6568	Remote Similarity	NPD3656	Approved
0.6564	Remote Similarity	NPD596	Approved
0.6564	Remote Similarity	NPD600	Approved
0.6562	Remote Similarity	NPD1669	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