NPASS Compound

Structure

NPC473640 OpenBabel07101719142D 55 58 0 0 1 0 0 0 0 0999 V2000 -3.5234 8.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1071 7.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6681 5.5149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3306 5.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1588 -0.8551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2183 0.5151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0998 6.6946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4036 4.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4036 5.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5376 4.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5376 6.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6787 6.7511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0787 3.8322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4115 3.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1327 5.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9133 -1.5545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1031 7.5688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3591 4.7921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2930 0.1359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3475 5.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7205 4.6562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6715 4.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6715 5.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2583 5.8438 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1072 3.5951 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4333 3.4973 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8983 -0.5546 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5020 0.7476 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2986 6.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0819 4.4335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0929 5.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1969 2.5992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2560 1.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7792 0.0565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9074 -0.4204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7205 6.2743 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4702 5.2246 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2984 6.1242 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7280 4.5204 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4931 2.4991 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8848 -0.3908 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9890 1.6210 0.0000 N 0 0 0 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 -1.0548 -2.0674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1347 7.0957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9554 4.9205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7620 6.0360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1951 2.5394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1813 1.1484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3548 -0.7612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6269 -1.3802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 11 25 2 0 0 0 0 12 26 2 0 0 0 0 14 47 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 24 1 0 0 0 0 18 24 2 0 0 0 0 18 40 1 0 0 0 0 19 48 1 0 0 0 0 23 7 1 6 0 0 0 23 33 1 0 0 0 0 23 41 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 40 1 0 0 0 0 27 15 1 6 0 0 0 27 35 1 0 0 0 0 27 42 1 0 0 0 0 28 16 1 6 0 0 0 28 36 1 0 0 0 0 28 43 1 0 0 0 0 29 17 1 6 0 0 0 29 34 1 0 0 0 0 29 44 1 0 0 0 0 30 19 1 6 0 0 0 30 39 1 0 0 0 0 30 45 1 0 0 0 0 31 13 1 6 0 0 0 31 37 1 0 0 0 0 31 47 1 0 0 0 0 32 22 1 6 0 0 0 32 38 1 0 0 0 0 32 46 1 0 0 0 0 33 42 2 3 0 0 0 33 49 1 0 0 0 0 34 41 2 3 0 0 0 34 50 1 0 0 0 0 35 43 2 3 0 0 0 35 51 1 0 0 0 0 36 46 2 3 0 0 0 36 52 1 0 0 0 0 37 44 2 3 0 0 0 37 53 1 0 0 0 0 38 45 2 3 0 0 0 38 54 1 0 0 0 0 39 47 1 0 0 0 0 39 55 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	766.44
Volume:	778.169
LogP:	2.419
LogD:	3.218
LogS:	-3.165
# Rotatable Bonds:	8
TPSA:	237.91
# H-Bond Aceptor:	16
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	5.634
Fsp3:	0.615
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.327
MDCK Permeability:	2.1420029952423647e-05
Pgp-inhibitor:	0.57
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.377
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.117

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	37.19786071777344%
Volume Distribution (VD):	0.556
Pgp-substrate:	41.955467224121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.594
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.138
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	1.51
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.997
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.834
Skin Sensitization:	0.153
Carcinogencity:	0.105
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC473640

Natural Product ID:	NPC473640
*Common Name:**	Integerrimide B
IUPAC Name:	(3S,6S,9S,12S,15S,18S,21S)-3-(hydroxymethyl)-18-(1H-indol-3-ylmethyl)-15-methyl-9,12-bis(2-methylpropyl)-6-propan-2-yl-1,4,7,10,13,16,19-heptazabicyclo[19.3.0]tetracosane-2,5,8,11,14,17,20-heptone
Synonyms:
Standard InCHIKey:	WFQBWZPTVRKYLS-HVEPFCGMSA-N
Standard InCHI:	InChI=1S/C39H58N8O8/c1-20(2)15-27-35(51)43-28(16-21(3)4)36(52)46-32(22(5)6)38(54)45-30(19-48)39(55)47-14-10-13-31(47)37(53)44-29(34(50)41-23(7)33(49)42-27)17-24-18-40-26-12-9-8-11-25(24)26/h8-9,11-12,18,20-23,27-32,40,48H,10,13-17,19H2,1-7H3,(H,41,50)(H,42,49)(H,43,51)(H,44,53)(H,45,54)(H,46,52)/t23-,27-,28-,29-,30-,31-,32-/m0/s1
SMILES:	CC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)N1)CC3=CNC4=CC=CC=C43)CO)C(C)C)CC(C)C)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447891
PubChem CID:	16059804
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO19811	Jatropha integerrima	Species	Euphorbiaceae	Eukaryota	latex	n.a.	n.a.	PMID[17067157]
NPO19811	Jatropha integerrima	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943622]
NPO19811	Jatropha integerrima	Species	Euphorbiaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4617	Cell Line	IPC-298	Homo sapiens	Activity	=	40.0	%	PMID[465774]
NPT1313	Cell Line	Capan-2	Homo sapiens	Inhibition	=	20.0	%	PMID[465774]

☑ 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 NPC473640 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	289
0.1-0.2	2023
0.2-0.3	17511
0.3-0.4	15214
0.4-0.5	2801
0.5-0.6	2728
0.6-0.7	1456
0.7-0.8	550
0.8-0.85	72
0.85-0.9	40
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9831	High Similarity	NPC475506
0.9777	High Similarity	NPC155143
0.9609	High Similarity	NPC100321
0.9459	High Similarity	NPC223791
0.9459	High Similarity	NPC107077
0.9432	High Similarity	NPC213629
0.9231	High Similarity	NPC171317
0.9144	High Similarity	NPC54420
0.9105	High Similarity	NPC75634
0.9076	High Similarity	NPC293917
0.9053	High Similarity	NPC320968
0.9048	High Similarity	NPC162860
0.8785	High Similarity	NPC94752
0.875	High Similarity	NPC314603
0.875	High Similarity	NPC478158
0.8737	High Similarity	NPC473376
0.8711	High Similarity	NPC31385
0.8711	High Similarity	NPC110602
0.8711	High Similarity	NPC75726
0.8634	High Similarity	NPC17059
0.8629	High Similarity	NPC160105
0.8624	High Similarity	NPC470497
0.8571	High Similarity	NPC54744
0.8528	High Similarity	NPC478157
0.8495	Intermediate Similarity	NPC243716
0.8492	Intermediate Similarity	NPC281049
0.847	Intermediate Similarity	NPC165495
0.847	Intermediate Similarity	NPC228835
0.8413	Intermediate Similarity	NPC478028
0.8396	Intermediate Similarity	NPC473763
0.8396	Intermediate Similarity	NPC117244
0.8374	Intermediate Similarity	NPC64216
0.8361	Intermediate Similarity	NPC233936
0.8342	Intermediate Similarity	NPC476874
0.8333	Intermediate Similarity	NPC478029
0.8315	Intermediate Similarity	NPC474561
0.8315	Intermediate Similarity	NPC49954
0.8308	Intermediate Similarity	NPC477714
0.8286	Intermediate Similarity	NPC469762
0.8251	Intermediate Similarity	NPC11126
0.8247	Intermediate Similarity	NPC193761
0.8229	Intermediate Similarity	NPC469785
0.8212	Intermediate Similarity	NPC54988
0.8207	Intermediate Similarity	NPC91179
0.8197	Intermediate Similarity	NPC59269
0.8191	Intermediate Similarity	NPC321708
0.8182	Intermediate Similarity	NPC474707
0.8182	Intermediate Similarity	NPC89987
0.8173	Intermediate Similarity	NPC323927
0.8173	Intermediate Similarity	NPC69843
0.8173	Intermediate Similarity	NPC326363
0.8171	Intermediate Similarity	NPC80597
0.8171	Intermediate Similarity	NPC70922
0.8171	Intermediate Similarity	NPC75540
0.8171	Intermediate Similarity	NPC211572
0.8171	Intermediate Similarity	NPC212376
0.8168	Intermediate Similarity	NPC477715
0.8152	Intermediate Similarity	NPC248041
0.8152	Intermediate Similarity	NPC283219
0.8152	Intermediate Similarity	NPC126709
0.8146	Intermediate Similarity	NPC282231
0.8142	Intermediate Similarity	NPC267885
0.8135	Intermediate Similarity	NPC470499
0.8114	Intermediate Similarity	NPC469763
0.8114	Intermediate Similarity	NPC73952
0.8114	Intermediate Similarity	NPC469760
0.8114	Intermediate Similarity	NPC469765
0.8114	Intermediate Similarity	NPC469786
0.8114	Intermediate Similarity	NPC25008
0.8114	Intermediate Similarity	NPC259644
0.8101	Intermediate Similarity	NPC311276
0.8098	Intermediate Similarity	NPC145885
0.8098	Intermediate Similarity	NPC14113
0.8098	Intermediate Similarity	NPC84827
0.8095	Intermediate Similarity	NPC173028
0.8095	Intermediate Similarity	NPC65215
0.809	Intermediate Similarity	NPC279918
0.8087	Intermediate Similarity	NPC149155
0.8087	Intermediate Similarity	NPC203468
0.8087	Intermediate Similarity	NPC110500
0.8085	Intermediate Similarity	NPC235684
0.8066	Intermediate Similarity	NPC201700
0.8066	Intermediate Similarity	NPC63751
0.8042	Intermediate Similarity	NPC204565
0.8042	Intermediate Similarity	NPC317030
0.8032	Intermediate Similarity	NPC15102
0.8029	Intermediate Similarity	NPC24370
0.8029	Intermediate Similarity	NPC319232
0.8019	Intermediate Similarity	NPC325976
0.801	Intermediate Similarity	NPC300183
0.8	Intermediate Similarity	NPC40779
0.8	Intermediate Similarity	NPC194640
0.799	Intermediate Similarity	NPC79386
0.7989	Intermediate Similarity	NPC469938
0.7979	Intermediate Similarity	NPC294693
0.7971	Intermediate Similarity	NPC155444
0.7962	Intermediate Similarity	NPC474877
0.7962	Intermediate Similarity	NPC475969
0.7962	Intermediate Similarity	NPC475859
0.795	Intermediate Similarity	NPC314957
0.7933	Intermediate Similarity	NPC230869
0.7927	Intermediate Similarity	NPC474177
0.7926	Intermediate Similarity	NPC163055
0.7915	Intermediate Similarity	NPC470729
0.7915	Intermediate Similarity	NPC477176
0.7915	Intermediate Similarity	NPC477175
0.7915	Intermediate Similarity	NPC470730
0.7887	Intermediate Similarity	NPC63279
0.7887	Intermediate Similarity	NPC133366
0.7877	Intermediate Similarity	NPC477177
0.7869	Intermediate Similarity	NPC78020
0.7865	Intermediate Similarity	NPC95783
0.7854	Intermediate Similarity	NPC470732
0.7854	Intermediate Similarity	NPC471192
0.7854	Intermediate Similarity	NPC470731
0.785	Intermediate Similarity	NPC297642
0.7846	Intermediate Similarity	NPC11445
0.7842	Intermediate Similarity	NPC280290
0.784	Intermediate Similarity	NPC165743
0.7838	Intermediate Similarity	NPC472123
0.7822	Intermediate Similarity	NPC271862
0.7819	Intermediate Similarity	NPC16659
0.7807	Intermediate Similarity	NPC248454
0.7807	Intermediate Similarity	NPC68354
0.7807	Intermediate Similarity	NPC64436
0.7804	Intermediate Similarity	NPC323752
0.7795	Intermediate Similarity	NPC195239
0.7795	Intermediate Similarity	NPC157828
0.7794	Intermediate Similarity	NPC153980
0.7794	Intermediate Similarity	NPC6865
0.7783	Intermediate Similarity	NPC56109
0.7783	Intermediate Similarity	NPC191382
0.7778	Intermediate Similarity	NPC28945
0.7778	Intermediate Similarity	NPC71037
0.7772	Intermediate Similarity	NPC127677
0.7772	Intermediate Similarity	NPC258062
0.7771	Intermediate Similarity	NPC314372
0.7766	Intermediate Similarity	NPC265710
0.7766	Intermediate Similarity	NPC213468
0.7756	Intermediate Similarity	NPC229348
0.775	Intermediate Similarity	NPC98715
0.7745	Intermediate Similarity	NPC72956
0.7725	Intermediate Similarity	NPC300688
0.7723	Intermediate Similarity	NPC225821
0.7723	Intermediate Similarity	NPC46225
0.772	Intermediate Similarity	NPC175474
0.7716	Intermediate Similarity	NPC229332
0.7716	Intermediate Similarity	NPC262898
0.7713	Intermediate Similarity	NPC240088
0.7713	Intermediate Similarity	NPC151939
0.7713	Intermediate Similarity	NPC473380
0.7707	Intermediate Similarity	NPC471194
0.7707	Intermediate Similarity	NPC471193
0.7705	Intermediate Similarity	NPC102423
0.7701	Intermediate Similarity	NPC37423
0.7701	Intermediate Similarity	NPC275305
0.7697	Intermediate Similarity	NPC105818
0.7697	Intermediate Similarity	NPC24678
0.7676	Intermediate Similarity	NPC317430
0.7672	Intermediate Similarity	NPC219336
0.7667	Intermediate Similarity	NPC473317
0.7665	Intermediate Similarity	NPC179701
0.7659	Intermediate Similarity	NPC54981
0.7657	Intermediate Similarity	NPC190296
0.7656	Intermediate Similarity	NPC163421
0.7656	Intermediate Similarity	NPC308931
0.7656	Intermediate Similarity	NPC188387
0.7656	Intermediate Similarity	NPC99939
0.7653	Intermediate Similarity	NPC476491
0.7647	Intermediate Similarity	NPC313791
0.7644	Intermediate Similarity	NPC48938
0.7644	Intermediate Similarity	NPC469358
0.7644	Intermediate Similarity	NPC472108
0.7644	Intermediate Similarity	NPC139291
0.7633	Intermediate Similarity	NPC313640
0.7626	Intermediate Similarity	NPC227582
0.7624	Intermediate Similarity	NPC285469
0.7621	Intermediate Similarity	NPC151976
0.7621	Intermediate Similarity	NPC87856
0.7619	Intermediate Similarity	NPC183662
0.7619	Intermediate Similarity	NPC217372
0.7619	Intermediate Similarity	NPC15573
0.7617	Intermediate Similarity	NPC315555
0.7611	Intermediate Similarity	NPC200214
0.7604	Intermediate Similarity	NPC472294
0.76	Intermediate Similarity	NPC252338
0.76	Intermediate Similarity	NPC469766
0.7596	Intermediate Similarity	NPC204491
0.7596	Intermediate Similarity	NPC131718
0.7596	Intermediate Similarity	NPC132211
0.7596	Intermediate Similarity	NPC203614
0.7588	Intermediate Similarity	NPC52557
0.7585	Intermediate Similarity	NPC267965
0.7579	Intermediate Similarity	NPC176199
0.7579	Intermediate Similarity	NPC215795
0.7579	Intermediate Similarity	NPC55772
0.7576	Intermediate Similarity	NPC242872
0.7576	Intermediate Similarity	NPC263117
0.7576	Intermediate Similarity	NPC125181
0.7566	Intermediate Similarity	NPC314882

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 NPC473640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	485
0.2-0.3	969
0.3-0.4	1665
0.4-0.5	2555
0.5-0.6	2333
0.6-0.7	831
0.7-0.8	117
0.8-0.85	21
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.914	High Similarity	NPD8272	Phase 2
0.9076	High Similarity	NPD7621	Clinical (unspecified phase)
0.8842	High Similarity	NPD8493	Clinical (unspecified phase)
0.8427	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.8407	Intermediate Similarity	NPD6595	Phase 3
0.8376	Intermediate Similarity	NPD7470	Discontinued
0.8342	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.8342	Intermediate Similarity	NPD7970	Approved
0.8289	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8283	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.8265	Intermediate Similarity	NPD8322	Phase 2
0.8263	Intermediate Similarity	NPD7944	Discontinued
0.8259	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.8216	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8128	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD2095	Phase 2
0.8118	Intermediate Similarity	NPD2092	Phase 2
0.8118	Intermediate Similarity	NPD2094	Phase 2
0.8116	Intermediate Similarity	NPD7711	Discontinued
0.8112	Intermediate Similarity	NPD8072	Approved
0.8087	Intermediate Similarity	NPD482	Approved
0.8077	Intermediate Similarity	NPD7731	Approved
0.8077	Intermediate Similarity	NPD7730	Approved
0.8075	Intermediate Similarity	NPD2096	Phase 2
0.8075	Intermediate Similarity	NPD2091	Phase 2
0.8068	Intermediate Similarity	NPD7271	Approved
0.8043	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD8431	Approved
0.8032	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7824	Approved
0.796	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.794	Intermediate Similarity	NPD7957	Phase 1
0.794	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD750	Phase 2
0.7919	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD2144	Approved
0.7887	Intermediate Similarity	NPD7952	Approved
0.7887	Intermediate Similarity	NPD7619	Phase 3
0.7887	Intermediate Similarity	NPD7791	Approved
0.7887	Intermediate Similarity	NPD7950	Approved
0.7887	Intermediate Similarity	NPD7789	Approved
0.7887	Intermediate Similarity	NPD7953	Approved
0.7887	Intermediate Similarity	NPD7951	Approved
0.7887	Intermediate Similarity	NPD7790	Approved
0.7887	Intermediate Similarity	NPD7618	Phase 3
0.7882	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD8073	Approved
0.7872	Intermediate Similarity	NPD3038	Discontinued
0.7861	Intermediate Similarity	NPD4079	Approved
0.7861	Intermediate Similarity	NPD4076	Approved
0.7853	Intermediate Similarity	NPD3961	Discontinued
0.7819	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD3506	Approved
0.7807	Intermediate Similarity	NPD3505	Approved
0.7783	Intermediate Similarity	NPD7781	Approved
0.7783	Intermediate Similarity	NPD7780	Approved
0.7772	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD8093	Discontinued
0.7696	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4075	Phase 2
0.7644	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5426	Phase 3
0.7621	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7585	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7948	Phase 1
0.7526	Intermediate Similarity	NPD6217	Discontinued
0.7523	Intermediate Similarity	NPD7603	Discontinued
0.7513	Intermediate Similarity	NPD5065	Approved
0.75	Intermediate Similarity	NPD8094	Discontinued
0.7487	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD786	Approved
0.7451	Intermediate Similarity	NPD8115	Approved
0.7451	Intermediate Similarity	NPD8114	Approved
0.745	Intermediate Similarity	NPD6664	Approved
0.7426	Intermediate Similarity	NPD4601	Approved
0.7426	Intermediate Similarity	NPD4600	Approved
0.7415	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2511	Approved
0.7403	Intermediate Similarity	NPD2172	Phase 1
0.7396	Intermediate Similarity	NPD8386	Phase 2
0.7394	Intermediate Similarity	NPD4640	Approved
0.7394	Intermediate Similarity	NPD4639	Approved
0.7394	Intermediate Similarity	NPD4638	Approved
0.7389	Intermediate Similarity	NPD7817	Phase 1
0.7385	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4181	Approved
0.7337	Intermediate Similarity	NPD6665	Discontinued
0.733	Intermediate Similarity	NPD4128	Approved
0.733	Intermediate Similarity	NPD7001	Phase 3
0.7323	Intermediate Similarity	NPD3321	Discontinued
0.7314	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8257	Approved
0.7311	Intermediate Similarity	NPD8256	Approved
0.7311	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5017	Discontinued
0.7303	Intermediate Similarity	NPD1722	Approved
0.7302	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8169	Discontinued
0.7269	Intermediate Similarity	NPD7717	Approved
0.7269	Intermediate Similarity	NPD7716	Approved
0.7255	Intermediate Similarity	NPD484	Approved
0.7253	Intermediate Similarity	NPD3100	Discontinued
0.7249	Intermediate Similarity	NPD2642	Approved
0.7249	Intermediate Similarity	NPD2639	Approved
0.7234	Intermediate Similarity	NPD5138	Approved
0.7234	Intermediate Similarity	NPD5140	Approved
0.7231	Intermediate Similarity	NPD8408	Discontinued
0.722	Intermediate Similarity	NPD7727	Phase 2
0.7208	Intermediate Similarity	NPD5555	Phase 1
0.7206	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6999	Discontinued
0.7202	Intermediate Similarity	NPD8289	Discontinued
0.7196	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8026	Phase 1
0.7179	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2509	Approved
0.7177	Intermediate Similarity	NPD7665	Phase 2
0.7177	Intermediate Similarity	NPD2510	Approved
0.7177	Intermediate Similarity	NPD7666	Phase 3
0.7176	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD1326	Approved
0.7173	Intermediate Similarity	NPD1325	Approved
0.7172	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5487	Phase 1
0.7136	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8021	Approved
0.7136	Intermediate Similarity	NPD8020	Approved
0.7131	Intermediate Similarity	NPD8284	Discontinued
0.7129	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD802	Phase 2
0.7129	Intermediate Similarity	NPD1038	Approved
0.7122	Intermediate Similarity	NPD6249	Phase 2
0.7122	Intermediate Similarity	NPD6248	Phase 2
0.712	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5901	Discontinued
0.7107	Intermediate Similarity	NPD5596	Phase 2
0.7104	Intermediate Similarity	NPD4702	Approved
0.7104	Intermediate Similarity	NPD4703	Approved
0.7104	Intermediate Similarity	NPD8374	Phase 3
0.71	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD8123	Approved
0.7077	Intermediate Similarity	NPD8122	Approved
0.7068	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4499	Approved
0.7053	Intermediate Similarity	NPD8129	Discovery
0.7053	Intermediate Similarity	NPD3323	Discontinued
0.7047	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1404	Approved
0.7037	Intermediate Similarity	NPD1403	Approved
0.7031	Intermediate Similarity	NPD2640	Approved
0.7031	Intermediate Similarity	NPD5021	Discontinued
0.7031	Intermediate Similarity	NPD2641	Approved
0.703	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4463	Approved
0.7027	Intermediate Similarity	NPD4462	Approved
0.7026	Intermediate Similarity	NPD6044	Discontinued
0.7	Intermediate Similarity	NPD7026	Phase 2
0.7	Intermediate Similarity	NPD6771	Discontinued
0.6995	Remote Similarity	NPD3404	Approved
0.6991	Remote Similarity	NPD5818	Discontinued
0.6985	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1096	Discontinued
0.6982	Remote Similarity	NPD5559	Phase 2
0.6978	Remote Similarity	NPD8329	Phase 3
0.6978	Remote Similarity	NPD3717	Discontinued
0.697	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8250	Phase 2
0.6968	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1392	Approved
0.6963	Remote Similarity	NPD3583	Phase 2
0.6959	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3117	Approved
0.6959	Remote Similarity	NPD3116	Approved
0.6957	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6173	Approved
0.6954	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8098	Approved
0.6952	Remote Similarity	NPD2837	Discontinued
0.6944	Remote Similarity	NPD5612	Discontinued
0.6943	Remote Similarity	NPD2844	Phase 3
0.6942	Remote Similarity	NPD5003	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