NPASS Compound

Structure

CID298186 OpenBabel06191716102D 24 28 0 0 1 0 0 0 0 0999 V2000 -1.0895 -4.1676 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 -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 -0.5789 -2.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 -1.1235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4985 -2.1195 0.0000 C 0 0 2 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 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 -0.6761 0.7368 0.0000 O 0 0 0 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 -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 22 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 5 19 1 0 0 0 0 6 19 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 1 0 0 0 17 20 1 1 0 0 0 18 4 1 6 0 0 0 18 19 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	331.14
Volume:	321.504
LogP:	0.511
LogD:	0.933
LogS:	-1.513
# Rotatable Bonds:	1
TPSA:	70.98
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	5.074
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:	-5.444
MDCK Permeability:	4.063565211254172e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.248
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.356
Plasma Protein Binding (PPB):	22.986730575561523%
Volume Distribution (VD):	2.71
Pgp-substrate:	61.34403991699219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.691
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.322
CYP2D6-inhibitor:	0.348
CYP2D6-substrate:	0.416
CYP3A4-inhibitor:	0.544
CYP3A4-substrate:	0.738

ADMET: Excretion

Clearance (CL):	9.782
Half-life (T1/2):	0.956

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.659
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.143
Rat Oral Acute Toxicity:	0.755
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.1
Carcinogencity:	0.909
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC298186

Natural Product ID:	NPC298186
*Common Name:**	AZWNRVNQMXFTSX-AKHDSKFASA-N
IUPAC Name:	n.a.
Synonyms:	Cephalotaxine Beta-N-Oxide
Standard InCHIKey:	AZWNRVNQMXFTSX-AKHDSKFASA-N
Standard InCHI:	InChI=1S/C18H21NO5/c1-22-15-9-18-4-2-5-19(18,21)6-3-11-7-13-14(24-10-23-13)8-12(11)16(18)17(15)20/h7-9,16-17,20H,2-6,10H2,1H3/t16-,17-,18+,19-/m1/s1
SMILES:	COC1=C[C@]23[C@@H]([C@@H]1O)c1cc4OCOc4cc1CCN3(=O)CCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464200
PubChem CID:	10404434
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	=	14.0	ug.mL-1	PMID[539052]

☑ 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 NPC298186 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	253
0.1-0.2	1291
0.2-0.3	4793
0.3-0.4	12855
0.4-0.5	7960
0.5-0.6	11540
0.6-0.7	3236
0.7-0.8	677
0.8-0.85	51
0.85-0.9	33
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC301189
0.9809	High Similarity	NPC57272
0.9057	High Similarity	NPC165797
0.8834	High Similarity	NPC476002
0.8554	High Similarity	NPC100566
0.8443	Intermediate Similarity	NPC181653
0.8443	Intermediate Similarity	NPC190332
0.8364	Intermediate Similarity	NPC4304
0.8263	Intermediate Similarity	NPC320104
0.8256	Intermediate Similarity	NPC237044
0.8208	Intermediate Similarity	NPC474325
0.8202	Intermediate Similarity	NPC319549
0.8198	Intermediate Similarity	NPC187678
0.8198	Intermediate Similarity	NPC304675
0.8187	Intermediate Similarity	NPC225597
0.8187	Intermediate Similarity	NPC477640
0.8187	Intermediate Similarity	NPC470739
0.8176	Intermediate Similarity	NPC158148
0.8176	Intermediate Similarity	NPC58766
0.8176	Intermediate Similarity	NPC266176
0.8176	Intermediate Similarity	NPC475686
0.8176	Intermediate Similarity	NPC290759
0.8176	Intermediate Similarity	NPC82533
0.8161	Intermediate Similarity	NPC474745
0.8133	Intermediate Similarity	NPC475326
0.8129	Intermediate Similarity	NPC474475
0.8118	Intermediate Similarity	NPC252960
0.8047	Intermediate Similarity	NPC218614
0.8036	Intermediate Similarity	NPC205167
0.8036	Intermediate Similarity	NPC249274
0.8036	Intermediate Similarity	NPC215829
0.8036	Intermediate Similarity	NPC97072
0.8023	Intermediate Similarity	NPC311991
0.8023	Intermediate Similarity	NPC474746
0.8023	Intermediate Similarity	NPC475981
0.8	Intermediate Similarity	NPC148898
0.7989	Intermediate Similarity	NPC49353
0.7976	Intermediate Similarity	NPC92191
0.7976	Intermediate Similarity	NPC59028
0.7966	Intermediate Similarity	NPC233718
0.7943	Intermediate Similarity	NPC474470
0.7933	Intermediate Similarity	NPC230098
0.7907	Intermediate Similarity	NPC57812
0.7907	Intermediate Similarity	NPC474324
0.7879	Intermediate Similarity	NPC274026
0.7861	Intermediate Similarity	NPC475845
0.7861	Intermediate Similarity	NPC160570
0.7853	Intermediate Similarity	NPC244554
0.7829	Intermediate Similarity	NPC2314
0.7816	Intermediate Similarity	NPC474708
0.7811	Intermediate Similarity	NPC40389
0.7811	Intermediate Similarity	NPC148014
0.7811	Intermediate Similarity	NPC78359
0.7811	Intermediate Similarity	NPC315707
0.7811	Intermediate Similarity	NPC65490
0.7798	Intermediate Similarity	NPC78733
0.7797	Intermediate Similarity	NPC294790
0.7797	Intermediate Similarity	NPC15919
0.7797	Intermediate Similarity	NPC118633
0.7797	Intermediate Similarity	NPC148693
0.7791	Intermediate Similarity	NPC180306
0.7784	Intermediate Similarity	NPC133011
0.7784	Intermediate Similarity	NPC82285
0.7753	Intermediate Similarity	NPC99179
0.7751	Intermediate Similarity	NPC147091
0.7719	Intermediate Similarity	NPC18402
0.7714	Intermediate Similarity	NPC329911
0.7714	Intermediate Similarity	NPC75958
0.7688	Intermediate Similarity	NPC231198
0.7688	Intermediate Similarity	NPC76116
0.7679	Intermediate Similarity	NPC37272
0.7676	Intermediate Similarity	NPC33256
0.7661	Intermediate Similarity	NPC69360
0.7661	Intermediate Similarity	NPC111485
0.7657	Intermediate Similarity	NPC164429
0.7602	Intermediate Similarity	NPC129603
0.7586	Intermediate Similarity	NPC238530
0.7586	Intermediate Similarity	NPC232514
0.7586	Intermediate Similarity	NPC276944
0.7586	Intermediate Similarity	NPC247972
0.7582	Intermediate Similarity	NPC9867
0.7576	Intermediate Similarity	NPC130926
0.7574	Intermediate Similarity	NPC223124
0.7571	Intermediate Similarity	NPC65403
0.7545	Intermediate Similarity	NPC475959
0.7529	Intermediate Similarity	NPC124433
0.7529	Intermediate Similarity	NPC293871
0.7486	Intermediate Similarity	NPC199465
0.7486	Intermediate Similarity	NPC229166
0.7486	Intermediate Similarity	NPC128560
0.7473	Intermediate Similarity	NPC275132
0.7473	Intermediate Similarity	NPC248642
0.7471	Intermediate Similarity	NPC233029
0.7471	Intermediate Similarity	NPC270811
0.7471	Intermediate Similarity	NPC471073
0.7471	Intermediate Similarity	NPC210148
0.7459	Intermediate Similarity	NPC126284
0.7456	Intermediate Similarity	NPC223125
0.7453	Intermediate Similarity	NPC475828
0.7443	Intermediate Similarity	NPC124657
0.7442	Intermediate Similarity	NPC37205
0.7442	Intermediate Similarity	NPC160931
0.7442	Intermediate Similarity	NPC146288
0.7432	Intermediate Similarity	NPC156576
0.7416	Intermediate Similarity	NPC474953
0.7407	Intermediate Similarity	NPC7018
0.7403	Intermediate Similarity	NPC320223
0.7403	Intermediate Similarity	NPC114364
0.7401	Intermediate Similarity	NPC150879
0.7386	Intermediate Similarity	NPC54125
0.7386	Intermediate Similarity	NPC89199
0.7384	Intermediate Similarity	NPC216459
0.7384	Intermediate Similarity	NPC41178
0.7384	Intermediate Similarity	NPC138487
0.736	Intermediate Similarity	NPC182257
0.7348	Intermediate Similarity	NPC283999
0.7341	Intermediate Similarity	NPC234392
0.7341	Intermediate Similarity	NPC31311
0.7341	Intermediate Similarity	NPC477133
0.7341	Intermediate Similarity	NPC477132
0.7337	Intermediate Similarity	NPC59907
0.7337	Intermediate Similarity	NPC135538
0.7337	Intermediate Similarity	NPC428
0.7337	Intermediate Similarity	NPC37144
0.7337	Intermediate Similarity	NPC147390
0.7337	Intermediate Similarity	NPC476571
0.7337	Intermediate Similarity	NPC246587
0.7337	Intermediate Similarity	NPC24233
0.7333	Intermediate Similarity	NPC228040
0.733	Intermediate Similarity	NPC59567
0.732	Intermediate Similarity	NPC80472
0.7308	Intermediate Similarity	NPC477560
0.7303	Intermediate Similarity	NPC304846
0.7303	Intermediate Similarity	NPC210918
0.7294	Intermediate Similarity	NPC211296
0.7288	Intermediate Similarity	NPC167546
0.7288	Intermediate Similarity	NPC302527
0.7288	Intermediate Similarity	NPC16805
0.7287	Intermediate Similarity	NPC94499
0.7283	Intermediate Similarity	NPC116284
0.7278	Intermediate Similarity	NPC191376
0.7278	Intermediate Similarity	NPC179825
0.7278	Intermediate Similarity	NPC321505
0.7263	Intermediate Similarity	NPC83198
0.7263	Intermediate Similarity	NPC204908
0.7262	Intermediate Similarity	NPC185838
0.7258	Intermediate Similarity	NPC162694
0.7258	Intermediate Similarity	NPC214116
0.7257	Intermediate Similarity	NPC477080
0.7251	Intermediate Similarity	NPC151895
0.7251	Intermediate Similarity	NPC97221
0.7251	Intermediate Similarity	NPC220858
0.7251	Intermediate Similarity	NPC88249
0.7251	Intermediate Similarity	NPC192768
0.7247	Intermediate Similarity	NPC24264
0.7247	Intermediate Similarity	NPC476432
0.7241	Intermediate Similarity	NPC323443
0.7241	Intermediate Similarity	NPC180756
0.7232	Intermediate Similarity	NPC233650
0.7228	Intermediate Similarity	NPC476574
0.7228	Intermediate Similarity	NPC474607
0.7228	Intermediate Similarity	NPC477561
0.7228	Intermediate Similarity	NPC312918
0.7228	Intermediate Similarity	NPC155442
0.7222	Intermediate Similarity	NPC259742
0.7222	Intermediate Similarity	NPC104077
0.7222	Intermediate Similarity	NPC219671
0.7222	Intermediate Similarity	NPC97316
0.7222	Intermediate Similarity	NPC147616
0.7207	Intermediate Similarity	NPC247389
0.7207	Intermediate Similarity	NPC210140
0.7207	Intermediate Similarity	NPC298979
0.7195	Intermediate Similarity	NPC131204
0.7195	Intermediate Similarity	NPC174191
0.7195	Intermediate Similarity	NPC301050
0.7193	Intermediate Similarity	NPC477565
0.7193	Intermediate Similarity	NPC103379
0.7193	Intermediate Similarity	NPC44869
0.7191	Intermediate Similarity	NPC225774
0.7191	Intermediate Similarity	NPC24465
0.7191	Intermediate Similarity	NPC134858
0.7189	Intermediate Similarity	NPC474650
0.7184	Intermediate Similarity	NPC193949
0.7184	Intermediate Similarity	NPC2413
0.7184	Intermediate Similarity	NPC469817
0.7184	Intermediate Similarity	NPC93593
0.7184	Intermediate Similarity	NPC295691
0.7184	Intermediate Similarity	NPC127674
0.7184	Intermediate Similarity	NPC278799
0.7184	Intermediate Similarity	NPC276588
0.7184	Intermediate Similarity	NPC207757
0.7184	Intermediate Similarity	NPC39701
0.7184	Intermediate Similarity	NPC249797
0.7184	Intermediate Similarity	NPC5238
0.7184	Intermediate Similarity	NPC204828
0.7184	Intermediate Similarity	NPC184026
0.7184	Intermediate Similarity	NPC110416
0.7184	Intermediate Similarity	NPC54379
0.7184	Intermediate Similarity	NPC172765
0.7184	Intermediate Similarity	NPC189266

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 NPC298186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	642
0.2-0.3	1291
0.3-0.4	2620
0.4-0.5	2501
0.5-0.6	1380
0.6-0.7	479
0.7-0.8	68
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8202	Intermediate Similarity	NPD7296	Approved
0.7811	Intermediate Similarity	NPD2563	Approved
0.7811	Intermediate Similarity	NPD2560	Approved
0.7544	Intermediate Similarity	NPD2977	Approved
0.7544	Intermediate Similarity	NPD2978	Approved
0.7543	Intermediate Similarity	NPD6071	Discontinued
0.75	Intermediate Similarity	NPD2970	Approved
0.75	Intermediate Similarity	NPD2969	Approved
0.741	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4236	Phase 3
0.7394	Intermediate Similarity	NPD4237	Approved
0.736	Intermediate Similarity	NPD27	Approved
0.736	Intermediate Similarity	NPD2489	Approved
0.7353	Intermediate Similarity	NPD4210	Discontinued
0.7345	Intermediate Similarity	NPD3051	Approved
0.7326	Intermediate Similarity	NPD4772	Phase 2
0.7326	Intermediate Similarity	NPD4773	Phase 2
0.7305	Intermediate Similarity	NPD5241	Discontinued
0.725	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5772	Approved
0.7241	Intermediate Similarity	NPD5773	Approved
0.7135	Intermediate Similarity	NPD7313	Approved
0.7135	Intermediate Similarity	NPD7311	Approved
0.7135	Intermediate Similarity	NPD7312	Approved
0.7135	Intermediate Similarity	NPD7310	Approved
0.7126	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7309	Approved
0.7083	Intermediate Similarity	NPD3060	Approved
0.7072	Intermediate Similarity	NPD4481	Phase 3
0.7066	Intermediate Similarity	NPD1375	Discontinued
0.7059	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7280	Phase 3
0.7043	Intermediate Similarity	NPD7281	Phase 3
0.7012	Intermediate Similarity	NPD2238	Phase 2
0.7006	Intermediate Similarity	NPD2161	Phase 2
0.6977	Remote Similarity	NPD4584	Approved
0.6962	Remote Similarity	NPD3705	Approved
0.6949	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4663	Approved
0.6895	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7906	Approved
0.6882	Remote Similarity	NPD4162	Approved
0.6879	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4578	Approved
0.6862	Remote Similarity	NPD4577	Approved
0.6857	Remote Similarity	NPD3686	Approved
0.6857	Remote Similarity	NPD3687	Approved
0.6856	Remote Similarity	NPD5582	Discontinued
0.6833	Remote Similarity	NPD7833	Phase 2
0.6833	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7831	Phase 2
0.6818	Remote Similarity	NPD4005	Discontinued
0.6813	Remote Similarity	NPD6107	Approved
0.6802	Remote Similarity	NPD2677	Approved
0.68	Remote Similarity	NPD3639	Approved
0.68	Remote Similarity	NPD3640	Phase 3
0.68	Remote Similarity	NPD3641	Approved
0.6793	Remote Similarity	NPD2898	Approved
0.6786	Remote Similarity	NPD6895	Approved
0.6786	Remote Similarity	NPD6896	Approved
0.6784	Remote Similarity	NPD5177	Phase 3
0.6776	Remote Similarity	NPD4010	Discontinued
0.6768	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7124	Phase 2
0.6747	Remote Similarity	NPD2674	Phase 3
0.674	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5604	Discontinued
0.6737	Remote Similarity	NPD8053	Approved
0.6737	Remote Similarity	NPD8054	Approved
0.6705	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7298	Approved
0.6701	Remote Similarity	NPD4420	Approved
0.6687	Remote Similarity	NPD3145	Approved
0.6687	Remote Similarity	NPD3144	Approved
0.6686	Remote Similarity	NPD6111	Discontinued
0.6685	Remote Similarity	NPD6876	Approved
0.6685	Remote Similarity	NPD6875	Approved
0.6667	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1357	Approved
0.665	Remote Similarity	NPD5006	Approved
0.665	Remote Similarity	NPD5005	Approved
0.6649	Remote Similarity	NPD2488	Approved
0.6649	Remote Similarity	NPD2490	Approved
0.6648	Remote Similarity	NPD52	Approved
0.6648	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7526	Approved
0.6647	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6843	Phase 3
0.6632	Remote Similarity	NPD6841	Approved
0.6632	Remote Similarity	NPD6842	Approved
0.6629	Remote Similarity	NPD4017	Approved
0.6628	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2492	Phase 1
0.6625	Remote Similarity	NPD2667	Approved
0.6625	Remote Similarity	NPD2668	Approved
0.6611	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6030	Approved
0.661	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6031	Approved
0.6605	Remote Similarity	NPD2230	Approved
0.6605	Remote Similarity	NPD2233	Approved
0.6605	Remote Similarity	NPD2232	Approved
0.6602	Remote Similarity	NPD7827	Phase 1
0.6596	Remote Similarity	NPD8156	Discontinued
0.6596	Remote Similarity	NPD5313	Approved
0.6596	Remote Similarity	NPD5312	Approved
0.6595	Remote Similarity	NPD4166	Phase 2
0.6591	Remote Similarity	NPD4123	Phase 3
0.6591	Remote Similarity	NPD3158	Phase 1
0.6591	Remote Similarity	NPD3157	Approved
0.6587	Remote Similarity	NPD5718	Phase 2
0.6587	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4585	Approved
0.6571	Remote Similarity	NPD6666	Approved
0.6571	Remote Similarity	NPD6667	Approved
0.6567	Remote Similarity	NPD3057	Approved
0.6567	Remote Similarity	NPD3533	Approved
0.6567	Remote Similarity	NPD2972	Approved
0.6564	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4055	Discovery
0.6556	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5090	Approved
0.6556	Remote Similarity	NPD5089	Approved
0.6556	Remote Similarity	NPD7110	Phase 1
0.6552	Remote Similarity	NPD6331	Phase 2
0.6548	Remote Similarity	NPD1130	Approved
0.6548	Remote Similarity	NPD1136	Approved
0.6548	Remote Similarity	NPD1132	Approved
0.6546	Remote Similarity	NPD3398	Discontinued
0.6543	Remote Similarity	NPD8251	Approved
0.6543	Remote Similarity	NPD8252	Approved
0.6543	Remote Similarity	NPD8099	Discontinued
0.6536	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1774	Approved
0.6526	Remote Similarity	NPD7007	Discovery
0.6519	Remote Similarity	NPD37	Approved
0.651	Remote Similarity	NPD2971	Approved
0.651	Remote Similarity	NPD2968	Approved
0.6503	Remote Similarity	NPD4965	Approved
0.6503	Remote Similarity	NPD4966	Approved
0.6503	Remote Similarity	NPD4967	Phase 2
0.6497	Remote Similarity	NPD4739	Approved
0.6495	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD598	Approved
0.6488	Remote Similarity	NPD597	Approved
0.6488	Remote Similarity	NPD601	Approved
0.6486	Remote Similarity	NPD3365	Discontinued
0.6486	Remote Similarity	NPD4666	Phase 3
0.6485	Remote Similarity	NPD3448	Approved
0.6485	Remote Similarity	NPD2491	Approved
0.6461	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD4108	Discontinued
0.6449	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6723	Discontinued
0.6437	Remote Similarity	NPD7037	Approved
0.6436	Remote Similarity	NPD2494	Approved
0.6436	Remote Similarity	NPD3452	Approved
0.6436	Remote Similarity	NPD2493	Approved
0.6436	Remote Similarity	NPD3450	Approved
0.6433	Remote Similarity	NPD823	Approved
0.6433	Remote Similarity	NPD817	Approved
0.6433	Remote Similarity	NPD2653	Approved
0.6432	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5709	Phase 3
0.6432	Remote Similarity	NPD6234	Discontinued
0.6429	Remote Similarity	NPD3180	Approved
0.6429	Remote Similarity	NPD3027	Phase 3
0.6429	Remote Similarity	NPD3382	Approved
0.6429	Remote Similarity	NPD3179	Approved
0.6429	Remote Similarity	NPD3384	Approved
0.6429	Remote Similarity	NPD3383	Approved
0.6425	Remote Similarity	NPD4727	Phase 1
0.6425	Remote Similarity	NPD2122	Discontinued
0.6425	Remote Similarity	NPD5976	Discontinued
0.6425	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4583	Approved
0.6422	Remote Similarity	NPD4582	Approved
0.642	Remote Similarity	NPD3692	Discontinued
0.6413	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6788	Approved
0.6412	Remote Similarity	NPD3061	Approved
0.6412	Remote Similarity	NPD3059	Approved
0.6412	Remote Similarity	NPD3620	Phase 2
0.6412	Remote Similarity	NPD3062	Approved
0.6412	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD4678	Approved
0.6409	Remote Similarity	NPD4675	Approved
0.6406	Remote Similarity	NPD7038	Approved
0.6406	Remote Similarity	NPD7039	Approved
0.6404	Remote Similarity	NPD1424	Approved
0.6404	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2973	Approved
0.64	Remote Similarity	NPD6674	Discontinued
0.64	Remote Similarity	NPD2975	Approved
0.64	Remote Similarity	NPD2974	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