NPASS Compound

Structure

NPC474475 OpenBabel07101718192D 22 26 0 0 1 0 0 0 0 0999 V2000 2.3033 1.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4022 2.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7440 0.1307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8078 -0.0683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8078 1.3103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6919 0.6615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4654 0.6210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4742 0.7496 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2109 0.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2109 0.9656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4047 0.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4047 0.9656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8429 0.4536 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2765 1.5239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6720 -0.1534 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6720 1.3954 0.0000 C 0 0 1 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 4.2763 0.1038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7301 2.3668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8850 -1.0866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0603 0.0634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0603 1.1786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 8 1 0 0 0 0 3 8 1 0 0 0 0 3 13 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 6 17 1 0 0 0 0 7 21 1 0 0 0 0 7 22 1 0 0 0 0 8 18 1 1 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 6 0 0 0 13 17 1 0 0 0 0 14 16 1 1 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	303.11
Volume:	286.912
LogP:	-0.278
LogD:	0.252
LogS:	-2.332
# Rotatable Bonds:	0
TPSA:	82.39
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	5.52
Fsp3:	0.5
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:	-5.285
MDCK Permeability:	2.9599175832117908e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.943
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.277
30% Bioavailability (F30%):	0.487

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.378
Plasma Protein Binding (PPB):	35.74835205078125%
Volume Distribution (VD):	1.455
Pgp-substrate:	73.89020538330078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.28
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.466
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.308
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.487

ADMET: Excretion

Clearance (CL):	5.545
Half-life (T1/2):	0.776

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.429
Carcinogencity:	0.902
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC474475

Natural Product ID:	NPC474475
*Common Name:**	Yemenine C
IUPAC Name:	n.a.
Synonyms:	Yemenine C
Standard InCHIKey:	RBDSXRNUXSBSRU-QJFMRHECSA-N
Standard InCHI:	InChI=1S/C16H17NO5/c18-8-1-2-16-10-5-12-11(21-7-22-12)4-9(10)15(20)17(6-14(16)19)13(16)3-8/h1-2,4-5,8,13-15,18-20H,3,6-7H2/t8-,13+,14-,15?,16-/m1/s1
SMILES:	C1C(C=CC23C1N(CC2O)C(C4=CC5=C(C=C34)OCO5)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469647
PubChem CID:	44559493
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004123] Crinine- and Haemanthamine-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
NPO23263	Crinum yemense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270564]
NPO23263	Crinum yemense	Species	Amaryllidaceae	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
Others	10

Activity Type	# Activity
Others	10

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	9.7	%	PMID[532698]
NPT27	Others	Unspecified	Activity	=	97.3	%	PMID[532698]
NPT2	Others	Unspecified	Inhibition	=	1.6	%	PMID[532698]
NPT27	Others	Unspecified	Activity	=	103.2	%	PMID[532698]
NPT2	Others	Unspecified	Inhibition	=	0.5	%	PMID[532698]
NPT27	Others	Unspecified	Activity	=	102.7	%	PMID[532698]
NPT2	Others	Unspecified	Inhibition	=	18.3	%	PMID[532698]
NPT27	Others	Unspecified	Activity	=	112.8	%	PMID[532698]
NPT2	Others	Unspecified	Inhibition	=	31.3	%	PMID[532698]
NPT27	Others	Unspecified	Activity	=	116.6	%	PMID[532698]

☑ 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 NPC474475 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	322
0.1-0.2	1289
0.2-0.3	4359
0.3-0.4	12035
0.4-0.5	7689
0.5-0.6	12625
0.6-0.7	3466
0.7-0.8	708
0.8-0.85	111
0.85-0.9	55
0.9-0.95	25
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC58766
0.9936	High Similarity	NPC225597
0.9936	High Similarity	NPC477640
0.9936	High Similarity	NPC475686
0.9936	High Similarity	NPC470739
0.9809	High Similarity	NPC266176
0.9809	High Similarity	NPC82533
0.9809	High Similarity	NPC158148
0.9809	High Similarity	NPC290759
0.9551	High Similarity	NPC215829
0.9551	High Similarity	NPC97072
0.9506	High Similarity	NPC474470
0.939	High Similarity	NPC244554
0.9375	High Similarity	NPC100566
0.9375	High Similarity	NPC181653
0.9375	High Similarity	NPC190332
0.9375	High Similarity	NPC252960
0.9308	High Similarity	NPC218614
0.9308	High Similarity	NPC320104
0.9259	High Similarity	NPC311991
0.925	High Similarity	NPC247972
0.9172	High Similarity	NPC78733
0.9146	High Similarity	NPC2314
0.9074	High Similarity	NPC476002
0.9036	High Similarity	NPC237044
0.9024	High Similarity	NPC75958
0.9	High Similarity	NPC92191
0.9	High Similarity	NPC59028
0.8982	High Similarity	NPC15919
0.8982	High Similarity	NPC474325
0.8976	High Similarity	NPC304675
0.8929	High Similarity	NPC474745
0.8875	High Similarity	NPC147091
0.883	High Similarity	NPC9867
0.8827	High Similarity	NPC4304
0.8788	High Similarity	NPC57812
0.8788	High Similarity	NPC474324
0.8772	High Similarity	NPC474746
0.8772	High Similarity	NPC475981
0.8757	High Similarity	NPC118633
0.8757	High Similarity	NPC294790
0.8757	High Similarity	NPC148693
0.875	High Similarity	NPC187678
0.8743	High Similarity	NPC65403
0.8735	High Similarity	NPC475845
0.8713	High Similarity	NPC248642
0.8712	High Similarity	NPC205167
0.8712	High Similarity	NPC249274
0.8688	High Similarity	NPC148898
0.8683	High Similarity	NPC474708
0.8671	High Similarity	NPC230098
0.8663	High Similarity	NPC156576
0.8639	High Similarity	NPC49353
0.8596	High Similarity	NPC126284
0.8571	High Similarity	NPC223124
0.8563	High Similarity	NPC150879
0.8562	High Similarity	NPC274026
0.8553	High Similarity	NPC475959
0.8528	High Similarity	NPC234392
0.8528	High Similarity	NPC31311
0.8497	Intermediate Similarity	NPC275132
0.8488	Intermediate Similarity	NPC99179
0.8457	Intermediate Similarity	NPC210148
0.8457	Intermediate Similarity	NPC233029
0.8447	Intermediate Similarity	NPC223125
0.8443	Intermediate Similarity	NPC238530
0.8443	Intermediate Similarity	NPC232514
0.8443	Intermediate Similarity	NPC276944
0.8424	Intermediate Similarity	NPC111485
0.8391	Intermediate Similarity	NPC233718
0.8383	Intermediate Similarity	NPC233650
0.8354	Intermediate Similarity	NPC138487
0.8354	Intermediate Similarity	NPC216459
0.8354	Intermediate Similarity	NPC41178
0.8352	Intermediate Similarity	NPC214116
0.8344	Intermediate Similarity	NPC133011
0.8344	Intermediate Similarity	NPC82285
0.8333	Intermediate Similarity	NPC134858
0.8333	Intermediate Similarity	NPC231198
0.8324	Intermediate Similarity	NPC114364
0.8324	Intermediate Similarity	NPC320223
0.8304	Intermediate Similarity	NPC57272
0.8303	Intermediate Similarity	NPC146288
0.8286	Intermediate Similarity	NPC476575
0.8286	Intermediate Similarity	NPC102760
0.8263	Intermediate Similarity	NPC165797
0.8253	Intermediate Similarity	NPC78359
0.8253	Intermediate Similarity	NPC148014
0.8253	Intermediate Similarity	NPC315707
0.8253	Intermediate Similarity	NPC65490
0.8253	Intermediate Similarity	NPC40389
0.825	Intermediate Similarity	NPC185838
0.825	Intermediate Similarity	NPC130926
0.8235	Intermediate Similarity	NPC247389
0.8235	Intermediate Similarity	NPC210918
0.8235	Intermediate Similarity	NPC210140
0.8225	Intermediate Similarity	NPC180306
0.821	Intermediate Similarity	NPC476571
0.821	Intermediate Similarity	NPC147390
0.821	Intermediate Similarity	NPC428
0.821	Intermediate Similarity	NPC135538
0.821	Intermediate Similarity	NPC246587
0.821	Intermediate Similarity	NPC24233
0.8208	Intermediate Similarity	NPC229166
0.8208	Intermediate Similarity	NPC199465
0.8208	Intermediate Similarity	NPC128560
0.8204	Intermediate Similarity	NPC69360
0.8204	Intermediate Similarity	NPC477080
0.8193	Intermediate Similarity	NPC37205
0.8193	Intermediate Similarity	NPC160931
0.8187	Intermediate Similarity	NPC160570
0.8176	Intermediate Similarity	NPC124657
0.8176	Intermediate Similarity	NPC219341
0.8176	Intermediate Similarity	NPC476432
0.8176	Intermediate Similarity	NPC24264
0.8166	Intermediate Similarity	NPC59567
0.8148	Intermediate Similarity	NPC476151
0.8148	Intermediate Similarity	NPC321505
0.8148	Intermediate Similarity	NPC191376
0.8148	Intermediate Similarity	NPC179825
0.8129	Intermediate Similarity	NPC298979
0.8129	Intermediate Similarity	NPC298186
0.8129	Intermediate Similarity	NPC301189
0.8118	Intermediate Similarity	NPC16805
0.8118	Intermediate Similarity	NPC169743
0.8118	Intermediate Similarity	NPC302527
0.8118	Intermediate Similarity	NPC225774
0.8118	Intermediate Similarity	NPC167546
0.8113	Intermediate Similarity	NPC328750
0.8113	Intermediate Similarity	NPC474915
0.8113	Intermediate Similarity	NPC188163
0.8113	Intermediate Similarity	NPC213206
0.8101	Intermediate Similarity	NPC141440
0.8089	Intermediate Similarity	NPC7018
0.8084	Intermediate Similarity	NPC180756
0.8084	Intermediate Similarity	NPC323443
0.8077	Intermediate Similarity	NPC33256
0.8066	Intermediate Similarity	NPC117717
0.8057	Intermediate Similarity	NPC283999
0.805	Intermediate Similarity	NPC314682
0.8049	Intermediate Similarity	NPC103379
0.8049	Intermediate Similarity	NPC477565
0.8047	Intermediate Similarity	NPC18402
0.8036	Intermediate Similarity	NPC475326
0.8036	Intermediate Similarity	NPC129603
0.8035	Intermediate Similarity	NPC329911
0.8034	Intermediate Similarity	NPC135772
0.8024	Intermediate Similarity	NPC189266
0.8024	Intermediate Similarity	NPC193949
0.8024	Intermediate Similarity	NPC469817
0.8024	Intermediate Similarity	NPC278799
0.8024	Intermediate Similarity	NPC54379
0.8024	Intermediate Similarity	NPC204828
0.8024	Intermediate Similarity	NPC110416
0.8024	Intermediate Similarity	NPC172765
0.8024	Intermediate Similarity	NPC5238
0.8024	Intermediate Similarity	NPC249797
0.8024	Intermediate Similarity	NPC127674
0.8024	Intermediate Similarity	NPC295691
0.8024	Intermediate Similarity	NPC184026
0.8024	Intermediate Similarity	NPC93593
0.8024	Intermediate Similarity	NPC207757
0.8024	Intermediate Similarity	NPC76079
0.8024	Intermediate Similarity	NPC276588
0.8024	Intermediate Similarity	NPC2413
0.8024	Intermediate Similarity	NPC39701
0.8012	Intermediate Similarity	NPC471073
0.8012	Intermediate Similarity	NPC270811
0.8012	Intermediate Similarity	NPC76116
0.8011	Intermediate Similarity	NPC63152
0.8	Intermediate Similarity	NPC220858
0.8	Intermediate Similarity	NPC88249
0.8	Intermediate Similarity	NPC192768
0.8	Intermediate Similarity	NPC97221
0.8	Intermediate Similarity	NPC477558
0.8	Intermediate Similarity	NPC151895
0.7988	Intermediate Similarity	NPC37144
0.7988	Intermediate Similarity	NPC59907
0.7988	Intermediate Similarity	NPC106786
0.7978	Intermediate Similarity	NPC116284
0.7966	Intermediate Similarity	NPC267408
0.7965	Intermediate Similarity	NPC264850
0.7965	Intermediate Similarity	NPC13916
0.7955	Intermediate Similarity	NPC241704
0.7953	Intermediate Similarity	NPC293871
0.7953	Intermediate Similarity	NPC124433
0.7941	Intermediate Similarity	NPC266753
0.7941	Intermediate Similarity	NPC160298
0.7941	Intermediate Similarity	NPC306902
0.7941	Intermediate Similarity	NPC232924
0.7941	Intermediate Similarity	NPC477559
0.7939	Intermediate Similarity	NPC60538
0.7939	Intermediate Similarity	NPC207824
0.7931	Intermediate Similarity	NPC474953
0.7927	Intermediate Similarity	NPC210437
0.7927	Intermediate Similarity	NPC106295
0.7927	Intermediate Similarity	NPC51957
0.7927	Intermediate Similarity	NPC16107
0.7927	Intermediate Similarity	NPC476144
0.7921	Intermediate Similarity	NPC476574

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 NPC474475 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	618
0.2-0.3	966
0.3-0.4	2319
0.4-0.5	2680
0.5-0.6	1679
0.6-0.7	582
0.7-0.8	113
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8284	Intermediate Similarity	NPD6071	Discontinued
0.8253	Intermediate Similarity	NPD2563	Approved
0.8253	Intermediate Similarity	NPD2560	Approved
0.8193	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2969	Approved
0.8129	Intermediate Similarity	NPD2970	Approved
0.8113	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD2978	Approved
0.8084	Intermediate Similarity	NPD2977	Approved
0.8072	Intermediate Similarity	NPD4773	Phase 2
0.8072	Intermediate Similarity	NPD4772	Phase 2
0.7978	Intermediate Similarity	NPD5582	Discontinued
0.7977	Intermediate Similarity	NPD2489	Approved
0.7977	Intermediate Similarity	NPD27	Approved
0.7965	Intermediate Similarity	NPD3051	Approved
0.7963	Intermediate Similarity	NPD5241	Discontinued
0.795	Intermediate Similarity	NPD4237	Approved
0.795	Intermediate Similarity	NPD4236	Phase 3
0.7927	Intermediate Similarity	NPD4584	Approved
0.7914	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4420	Approved
0.7889	Intermediate Similarity	NPD4663	Approved
0.787	Intermediate Similarity	NPD5773	Approved
0.787	Intermediate Similarity	NPD5772	Approved
0.7853	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD7906	Approved
0.7821	Intermediate Similarity	NPD4578	Approved
0.7821	Intermediate Similarity	NPD4577	Approved
0.7819	Intermediate Similarity	NPD5006	Approved
0.7819	Intermediate Similarity	NPD5005	Approved
0.7771	Intermediate Similarity	NPD4481	Phase 3
0.7771	Intermediate Similarity	NPD2898	Approved
0.7722	Intermediate Similarity	NPD7313	Approved
0.7722	Intermediate Similarity	NPD7311	Approved
0.7722	Intermediate Similarity	NPD7310	Approved
0.7722	Intermediate Similarity	NPD7312	Approved
0.768	Intermediate Similarity	NPD7309	Approved
0.765	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5604	Discontinued
0.7624	Intermediate Similarity	NPD7280	Phase 3
0.7624	Intermediate Similarity	NPD7281	Phase 3
0.76	Intermediate Similarity	NPD6107	Approved
0.7574	Intermediate Similarity	NPD4210	Discontinued
0.7529	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7833	Phase 2
0.7529	Intermediate Similarity	NPD4017	Approved
0.7529	Intermediate Similarity	NPD7831	Phase 2
0.7527	Intermediate Similarity	NPD7296	Approved
0.7515	Intermediate Similarity	NPD3641	Approved
0.7515	Intermediate Similarity	NPD3639	Approved
0.7515	Intermediate Similarity	NPD3060	Approved
0.7515	Intermediate Similarity	NPD3640	Phase 3
0.75	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8054	Approved
0.7486	Intermediate Similarity	NPD8053	Approved
0.7458	Intermediate Similarity	NPD4010	Discontinued
0.7444	Intermediate Similarity	NPD8156	Discontinued
0.7425	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6030	Approved
0.7412	Intermediate Similarity	NPD6031	Approved
0.7399	Intermediate Similarity	NPD7298	Approved
0.7396	Intermediate Similarity	NPD3450	Approved
0.7396	Intermediate Similarity	NPD3452	Approved
0.7389	Intermediate Similarity	NPD8099	Discontinued
0.7389	Intermediate Similarity	NPD8251	Approved
0.7389	Intermediate Similarity	NPD8252	Approved
0.7375	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2975	Approved
0.7368	Intermediate Similarity	NPD2974	Approved
0.7368	Intermediate Similarity	NPD3687	Approved
0.7368	Intermediate Similarity	NPD3686	Approved
0.7368	Intermediate Similarity	NPD2973	Approved
0.7363	Intermediate Similarity	NPD6297	Approved
0.7316	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD2494	Approved
0.7306	Intermediate Similarity	NPD2493	Approved
0.7305	Intermediate Similarity	NPD5177	Phase 3
0.7297	Intermediate Similarity	NPD6851	Approved
0.7297	Intermediate Similarity	NPD6853	Approved
0.7294	Intermediate Similarity	NPD4123	Phase 3
0.7289	Intermediate Similarity	NPD1375	Discontinued
0.7284	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1753	Discontinued
0.7273	Intermediate Similarity	NPD6788	Approved
0.7263	Intermediate Similarity	NPD4166	Phase 2
0.7256	Intermediate Similarity	NPD817	Approved
0.7256	Intermediate Similarity	NPD823	Approved
0.7254	Intermediate Similarity	NPD4580	Approved
0.7253	Intermediate Similarity	NPD5312	Approved
0.7253	Intermediate Similarity	NPD5313	Approved
0.7239	Intermediate Similarity	NPD2238	Phase 2
0.7231	Intermediate Similarity	NPD4002	Approved
0.7231	Intermediate Similarity	NPD4004	Approved
0.7225	Intermediate Similarity	NPD4005	Discontinued
0.722	Intermediate Similarity	NPD6997	Phase 2
0.7204	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4162	Approved
0.7196	Intermediate Similarity	NPD2490	Approved
0.7196	Intermediate Similarity	NPD2488	Approved
0.7194	Intermediate Similarity	NPD4583	Approved
0.7194	Intermediate Similarity	NPD4582	Approved
0.7152	Intermediate Similarity	NPD2492	Phase 1
0.7151	Intermediate Similarity	NPD2971	Approved
0.7151	Intermediate Similarity	NPD2968	Approved
0.7135	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6687	Approved
0.7127	Intermediate Similarity	NPD6688	Approved
0.7118	Intermediate Similarity	NPD3692	Discontinued
0.7118	Intermediate Similarity	NPD2677	Approved
0.7117	Intermediate Similarity	NPD5718	Phase 2
0.7114	Intermediate Similarity	NPD7827	Phase 1
0.7113	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2122	Discontinued
0.711	Intermediate Similarity	NPD4727	Phase 1
0.7108	Intermediate Similarity	NPD6896	Approved
0.7108	Intermediate Similarity	NPD6895	Approved
0.7105	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7047	Phase 3
0.7093	Intermediate Similarity	NPD1424	Approved
0.7089	Intermediate Similarity	NPD3705	Approved
0.7088	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4675	Approved
0.7086	Intermediate Similarity	NPD4678	Approved
0.7076	Intermediate Similarity	NPD7124	Phase 2
0.7066	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5677	Discontinued
0.7052	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD52	Approved
0.7052	Intermediate Similarity	NPD7526	Approved
0.7043	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3124	Discontinued
0.7029	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3885	Approved
0.7019	Intermediate Similarity	NPD4103	Phase 2
0.7019	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5976	Discontinued
0.7006	Intermediate Similarity	NPD3382	Approved
0.7006	Intermediate Similarity	NPD3383	Approved
0.7006	Intermediate Similarity	NPD3384	Approved
0.7006	Intermediate Similarity	NPD1357	Approved
0.7005	Intermediate Similarity	NPD3057	Approved
0.6994	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7007	Discovery
0.6983	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3845	Phase 1
0.697	Remote Similarity	NPD1132	Approved
0.697	Remote Similarity	NPD2674	Phase 3
0.697	Remote Similarity	NPD1136	Approved
0.697	Remote Similarity	NPD1130	Approved
0.6968	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6090	Discontinued
0.6944	Remote Similarity	NPD4055	Discovery
0.6941	Remote Similarity	NPD7037	Approved
0.6941	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2421	Approved
0.6936	Remote Similarity	NPD1774	Approved
0.6936	Remote Similarity	NPD2420	Approved
0.6928	Remote Similarity	NPD3061	Approved
0.6928	Remote Similarity	NPD3062	Approved
0.6928	Remote Similarity	NPD3109	Approved
0.6928	Remote Similarity	NPD3059	Approved
0.6928	Remote Similarity	NPD3110	Approved
0.6923	Remote Similarity	NPD7802	Discontinued
0.6923	Remote Similarity	NPD2161	Phase 2
0.6923	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3448	Approved
0.6919	Remote Similarity	NPD5160	Discontinued
0.6919	Remote Similarity	NPD2972	Approved
0.6919	Remote Similarity	NPD3533	Approved
0.6909	Remote Similarity	NPD597	Approved
0.6909	Remote Similarity	NPD601	Approved
0.6909	Remote Similarity	NPD598	Approved
0.6906	Remote Similarity	NPD5709	Phase 3
0.69	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2874	Phase 2
0.6897	Remote Similarity	NPD7020	Approved
0.6897	Remote Similarity	NPD5676	Approved
0.6897	Remote Similarity	NPD7019	Approved
0.6897	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4659	Approved
0.6882	Remote Similarity	NPD6042	Phase 2
0.6882	Remote Similarity	NPD42	Phase 2
0.6879	Remote Similarity	NPD3122	Phase 3
0.6879	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2904	Discontinued
0.6868	Remote Similarity	NPD4666	Phase 3
0.6862	Remote Similarity	NPD7039	Approved
0.6862	Remote Similarity	NPD7038	Approved
0.6859	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6072	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