NPASS Compound

Structure

CID213629 OpenBabel06191716002D 44 47 0 0 1 0 0 0 0 0999 V2000 3.7017 3.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 3.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3900 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5240 -3.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1953 -2.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2620 2.5054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9312 1.7623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2750 0.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2839 2.2975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6221 0.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4460 1.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9994 0.0349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1953 1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1658 -0.0548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 -3.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 3.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5240 -2.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3293 -1.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0613 0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9749 1.3464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6440 0.6033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3293 0.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3420 0.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8508 -3.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 2.3794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3420 -1.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6865 -2.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6713 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 1.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8204 2.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1440 -0.2627 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8204 -3.2057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6713 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6865 1.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 -2.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 2.2057 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 1.5088 -4.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3293 -3.4718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6561 0.1736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3420 2.4718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1625 3.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 -1.1736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 20 2 0 0 0 0 10 21 2 0 0 0 0 12 38 1 0 0 0 0 13 19 1 0 0 0 0 14 19 2 0 0 0 0 14 32 1 0 0 0 0 15 24 1 0 0 0 0 15 33 1 0 0 0 0 18 5 1 1 0 0 0 18 27 1 0 0 0 0 18 34 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 32 1 0 0 0 0 22 13 1 1 0 0 0 22 28 1 0 0 0 0 22 35 1 0 0 0 0 23 11 1 1 0 0 0 23 29 1 0 0 0 0 23 38 1 0 0 0 0 24 36 2 3 0 0 0 24 39 1 0 0 0 0 25 16 1 1 0 0 0 25 30 1 0 0 0 0 25 37 1 0 0 0 0 26 17 1 1 0 0 0 26 31 1 0 0 0 0 26 36 1 0 0 0 0 27 33 2 3 0 0 0 27 40 1 0 0 0 0 28 34 2 3 0 0 0 28 41 1 0 0 0 0 29 37 2 3 0 0 0 29 42 1 0 0 0 0 30 35 2 3 0 0 0 30 43 1 0 0 0 0 31 38 1 0 0 0 0 31 44 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	609.33
Volume:	613.86
LogP:	1.499
LogD:	1.956
LogS:	-3.668
# Rotatable Bonds:	4
TPSA:	181.6
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.286
Synthetic Accessibility Score:	4.78
Fsp3:	0.548
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:	-6.156
MDCK Permeability:	5.697281721950276e-06
Pgp-inhibitor:	0.816
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	60.26878356933594%
Volume Distribution (VD):	0.496
Pgp-substrate:	32.440914154052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.254
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.196
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	5.209
Half-life (T1/2):	0.815

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.907
Drug-inuced Liver Injury (DILI):	0.797
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.509
Skin Sensitization:	0.179
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.726

Download Data

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

Natural Product: NPC213629

Natural Product ID:	NPC213629
*Common Name:**	Segetalin A
IUPAC Name:	(3S,9S,12S,15S,18S)-12-(1H-indol-3-ylmethyl)-9-methyl-3,15-di(propan-2-yl)-1,4,7,10,13,16-hexazabicyclo[16.3.0]henicosane-2,5,8,11,14,17-hexone
Synonyms:
Standard InCHIKey:	YVUZOKYOUUCVBV-WJTDBPPMSA-N
Standard InCHI:	InChI=1S/C31H43N7O6/c1-16(2)25-30(43)35-22(13-19-14-32-21-10-7-6-9-20(19)21)28(41)34-18(5)27(40)33-15-24(39)36-26(17(3)4)31(44)38-12-8-11-23(38)29(42)37-25/h6-7,9-10,14,16-18,22-23,25-26,32H,8,11-13,15H2,1-5H3,(H,33,40)(H,34,41)(H,35,43)(H,36,39)(H,37,42)/t18-,22-,23-,25-,26-/m0/s1
SMILES:	OC1=N[C@@H](C(C)C)C(=O)N2CCC[C@H]2C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=NC1)O)C)O)Cc1c[nH]c2c1cccc2)O)C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL378333
PubChem CID:	10483858
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
NPO40525	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[9157189]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6752	Melandryum firmum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	54.4	mg	PMID[520382]

☑ 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 NPC213629 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	320
0.1-0.2	2558
0.2-0.3	19178
0.3-0.4	13193
0.4-0.5	2648
0.5-0.6	2495
0.6-0.7	1528
0.7-0.8	631
0.8-0.85	79
0.85-0.9	48
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9543	High Similarity	NPC171317
0.9489	High Similarity	NPC293917
0.9432	High Similarity	NPC473640
0.9382	High Similarity	NPC475506
0.9379	High Similarity	NPC100321
0.933	High Similarity	NPC155143
0.9302	High Similarity	NPC94752
0.9227	High Similarity	NPC473376
0.9138	High Similarity	NPC17059
0.9042	High Similarity	NPC160105
0.9027	High Similarity	NPC223791
0.9027	High Similarity	NPC107077
0.9022	High Similarity	NPC54420
0.8966	High Similarity	NPC228835
0.893	High Similarity	NPC320968
0.8925	High Similarity	NPC162860
0.8925	High Similarity	NPC478158
0.8883	High Similarity	NPC75634
0.8883	High Similarity	NPC75726
0.8883	High Similarity	NPC110602
0.8883	High Similarity	NPC31385
0.8857	High Similarity	NPC165495
0.8836	High Similarity	NPC54744
0.883	High Similarity	NPC314603
0.8736	High Similarity	NPC11126
0.8706	High Similarity	NPC49954
0.8706	High Similarity	NPC474561
0.8691	High Similarity	NPC478157
0.8686	High Similarity	NPC91179
0.8667	High Similarity	NPC473763
0.8667	High Similarity	NPC117244
0.8659	High Similarity	NPC321708
0.8653	High Similarity	NPC477714
0.8629	High Similarity	NPC283219
0.8629	High Similarity	NPC126709
0.8629	High Similarity	NPC248041
0.8621	High Similarity	NPC267885
0.8571	High Similarity	NPC14113
0.8571	High Similarity	NPC59269
0.8571	High Similarity	NPC145885
0.8571	High Similarity	NPC84827
0.8564	High Similarity	NPC243716
0.8563	High Similarity	NPC149155
0.8563	High Similarity	NPC110500
0.8563	High Similarity	NPC203468
0.8547	High Similarity	NPC235684
0.8529	High Similarity	NPC282231
0.8505	High Similarity	NPC477715
0.8503	High Similarity	NPC469763
0.8503	High Similarity	NPC259644
0.8503	High Similarity	NPC25008
0.8503	High Similarity	NPC469765
0.8503	High Similarity	NPC73952
0.8503	High Similarity	NPC469786
0.8503	High Similarity	NPC469760
0.8471	Intermediate Similarity	NPC279918
0.8452	Intermediate Similarity	NPC212376
0.8452	Intermediate Similarity	NPC75540
0.8452	Intermediate Similarity	NPC80597
0.8452	Intermediate Similarity	NPC70922
0.8452	Intermediate Similarity	NPC211572
0.8439	Intermediate Similarity	NPC63751
0.8427	Intermediate Similarity	NPC233936
0.8396	Intermediate Similarity	NPC470497
0.8389	Intermediate Similarity	NPC15102
0.8387	Intermediate Similarity	NPC470499
0.8372	Intermediate Similarity	NPC194640
0.8367	Intermediate Similarity	NPC281049
0.8353	Intermediate Similarity	NPC469762
0.8352	Intermediate Similarity	NPC469938
0.8333	Intermediate Similarity	NPC78020
0.8294	Intermediate Similarity	NPC469785
0.8276	Intermediate Similarity	NPC54988
0.8266	Intermediate Similarity	NPC311276
0.8258	Intermediate Similarity	NPC64436
0.8242	Intermediate Similarity	NPC474707
0.8227	Intermediate Similarity	NPC69843
0.8227	Intermediate Similarity	NPC326363
0.8212	Intermediate Similarity	NPC213468
0.8211	Intermediate Similarity	NPC193761
0.8205	Intermediate Similarity	NPC6865
0.8205	Intermediate Similarity	NPC153980
0.82	Intermediate Similarity	NPC155444
0.8167	Intermediate Similarity	NPC16659
0.8159	Intermediate Similarity	NPC64216
0.8158	Intermediate Similarity	NPC300183
0.8156	Intermediate Similarity	NPC248454
0.8154	Intermediate Similarity	NPC72956
0.8152	Intermediate Similarity	NPC65215
0.8152	Intermediate Similarity	NPC173028
0.8144	Intermediate Similarity	NPC314372
0.8138	Intermediate Similarity	NPC262898
0.8128	Intermediate Similarity	NPC294693
0.8125	Intermediate Similarity	NPC201700
0.8115	Intermediate Similarity	NPC476874
0.8112	Intermediate Similarity	NPC471194
0.8112	Intermediate Similarity	NPC471193
0.8111	Intermediate Similarity	NPC219336
0.8111	Intermediate Similarity	NPC265710
0.8098	Intermediate Similarity	NPC317030
0.8098	Intermediate Similarity	NPC204565
0.8087	Intermediate Similarity	NPC99939
0.8087	Intermediate Similarity	NPC308931
0.8085	Intermediate Similarity	NPC179701
0.8079	Intermediate Similarity	NPC319232
0.8079	Intermediate Similarity	NPC24370
0.8068	Intermediate Similarity	NPC325976
0.8059	Intermediate Similarity	NPC24678
0.8059	Intermediate Similarity	NPC105818
0.8057	Intermediate Similarity	NPC40779
0.8056	Intermediate Similarity	NPC473380
0.8056	Intermediate Similarity	NPC240088
0.8056	Intermediate Similarity	NPC217372
0.8056	Intermediate Similarity	NPC15573
0.8056	Intermediate Similarity	NPC183662
0.8042	Intermediate Similarity	NPC227582
0.8029	Intermediate Similarity	NPC478028
0.8024	Intermediate Similarity	NPC190296
0.8011	Intermediate Similarity	NPC55772
0.8	Intermediate Similarity	NPC191382
0.8	Intermediate Similarity	NPC56109
0.8	Intermediate Similarity	NPC314957
0.799	Intermediate Similarity	NPC471192
0.7989	Intermediate Similarity	NPC161861
0.7989	Intermediate Similarity	NPC230869
0.7989	Intermediate Similarity	NPC11445
0.7979	Intermediate Similarity	NPC474177
0.7978	Intermediate Similarity	NPC163055
0.7977	Intermediate Similarity	NPC285469
0.7971	Intermediate Similarity	NPC89987
0.797	Intermediate Similarity	NPC54981
0.7965	Intermediate Similarity	NPC200214
0.7956	Intermediate Similarity	NPC111275
0.7952	Intermediate Similarity	NPC478029
0.7951	Intermediate Similarity	NPC476491
0.7937	Intermediate Similarity	NPC195239
0.7937	Intermediate Similarity	NPC157828
0.7937	Intermediate Similarity	NPC133366
0.7927	Intermediate Similarity	NPC476073
0.7923	Intermediate Similarity	NPC71037
0.7917	Intermediate Similarity	NPC252338
0.7912	Intermediate Similarity	NPC248462
0.791	Intermediate Similarity	NPC475736
0.7906	Intermediate Similarity	NPC131887
0.7904	Intermediate Similarity	NPC469784
0.7904	Intermediate Similarity	NPC469779
0.7904	Intermediate Similarity	NPC469767
0.7904	Intermediate Similarity	NPC469768
0.7904	Intermediate Similarity	NPC469780
0.7904	Intermediate Similarity	NPC469783
0.7904	Intermediate Similarity	NPC469761
0.7892	Intermediate Similarity	NPC280290
0.7886	Intermediate Similarity	NPC135141
0.7886	Intermediate Similarity	NPC92796
0.7869	Intermediate Similarity	NPC469896
0.7857	Intermediate Similarity	NPC469766
0.7857	Intermediate Similarity	NPC323927
0.7849	Intermediate Similarity	NPC53947
0.7849	Intermediate Similarity	NPC62749
0.7847	Intermediate Similarity	NPC323752
0.7844	Intermediate Similarity	NPC73767
0.7841	Intermediate Similarity	NPC131718
0.7838	Intermediate Similarity	NPC472294
0.7837	Intermediate Similarity	NPC475969
0.7837	Intermediate Similarity	NPC475859
0.7837	Intermediate Similarity	NPC474877
0.7824	Intermediate Similarity	NPC159856
0.7824	Intermediate Similarity	NPC106771
0.7824	Intermediate Similarity	NPC205254
0.7824	Intermediate Similarity	NPC23420
0.7824	Intermediate Similarity	NPC470440
0.7824	Intermediate Similarity	NPC303820
0.7822	Intermediate Similarity	NPC473310
0.7819	Intermediate Similarity	NPC95783
0.7817	Intermediate Similarity	NPC71238
0.78	Intermediate Similarity	NPC229348
0.7797	Intermediate Similarity	NPC16667
0.7796	Intermediate Similarity	NPC163421
0.7796	Intermediate Similarity	NPC188387
0.779	Intermediate Similarity	NPC472123
0.7788	Intermediate Similarity	NPC477176
0.7788	Intermediate Similarity	NPC477175
0.7788	Intermediate Similarity	NPC470729
0.7788	Intermediate Similarity	NPC470730
0.7784	Intermediate Similarity	NPC52909
0.7784	Intermediate Similarity	NPC475935
0.7784	Intermediate Similarity	NPC94211
0.7778	Intermediate Similarity	NPC194411
0.7772	Intermediate Similarity	NPC300688
0.7772	Intermediate Similarity	NPC74413
0.7766	Intermediate Similarity	NPC166492
0.7766	Intermediate Similarity	NPC473362
0.7765	Intermediate Similarity	NPC49217
0.7762	Intermediate Similarity	NPC63279
0.776	Intermediate Similarity	NPC68354
0.776	Intermediate Similarity	NPC151939
0.776	Intermediate Similarity	NPC229332
0.7754	Intermediate Similarity	NPC315555
0.7751	Intermediate Similarity	NPC477177
0.7742	Intermediate Similarity	NPC477003

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 NPC213629 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	491
0.2-0.3	999
0.3-0.4	1599
0.4-0.5	2453
0.5-0.6	2292
0.6-0.7	955
0.7-0.8	135
0.8-0.85	36
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9489	High Similarity	NPD7621	Clinical (unspecified phase)
0.9126	High Similarity	NPD8493	Clinical (unspecified phase)
0.8913	High Similarity	NPD8272	Phase 2
0.8824	High Similarity	NPD4184	Clinical (unspecified phase)
0.8693	High Similarity	NPD5728	Clinical (unspecified phase)
0.8632	High Similarity	NPD7470	Discontinued
0.8588	High Similarity	NPD2092	Phase 2
0.8588	High Similarity	NPD2095	Phase 2
0.8588	High Similarity	NPD2094	Phase 2
0.858	High Similarity	NPD6595	Phase 3
0.8563	High Similarity	NPD482	Approved
0.8539	High Similarity	NPD2096	Phase 2
0.8539	High Similarity	NPD2091	Phase 2
0.8534	High Similarity	NPD8013	Clinical (unspecified phase)
0.8514	High Similarity	NPD749	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7970	Approved
0.84	Intermediate Similarity	NPD750	Phase 2
0.8392	Intermediate Similarity	NPD7271	Approved
0.8389	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.835	Intermediate Similarity	NPD7711	Discontinued
0.8324	Intermediate Similarity	NPD7944	Discontinued
0.8324	Intermediate Similarity	NPD7619	Phase 3
0.8324	Intermediate Similarity	NPD7618	Phase 3
0.8316	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD7731	Approved
0.8308	Intermediate Similarity	NPD7730	Approved
0.8299	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.829	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.829	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD7824	Approved
0.8197	Intermediate Similarity	NPD8431	Approved
0.8197	Intermediate Similarity	NPD3961	Discontinued
0.8158	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.8135	Intermediate Similarity	NPD8322	Phase 2
0.8135	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7791	Approved
0.8107	Intermediate Similarity	NPD7790	Approved
0.8107	Intermediate Similarity	NPD7950	Approved
0.8107	Intermediate Similarity	NPD7952	Approved
0.8107	Intermediate Similarity	NPD7789	Approved
0.8107	Intermediate Similarity	NPD7953	Approved
0.8107	Intermediate Similarity	NPD7951	Approved
0.8083	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.8083	Intermediate Similarity	NPD7957	Phase 1
0.8073	Intermediate Similarity	NPD8072	Approved
0.8056	Intermediate Similarity	NPD2144	Approved
0.8031	Intermediate Similarity	NPD5426	Phase 3
0.8022	Intermediate Similarity	NPD3038	Discontinued
0.8021	Intermediate Similarity	NPD8073	Approved
0.8	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7781	Approved
0.8	Intermediate Similarity	NPD4075	Phase 2
0.8	Intermediate Similarity	NPD7780	Approved
0.7967	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD8093	Discontinued
0.7919	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6664	Approved
0.7849	Intermediate Similarity	NPD6217	Discontinued
0.7845	Intermediate Similarity	NPD5065	Approved
0.7844	Intermediate Similarity	NPD786	Approved
0.7817	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7603	Discontinued
0.7814	Intermediate Similarity	NPD4079	Approved
0.7814	Intermediate Similarity	NPD4076	Approved
0.7801	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD3505	Approved
0.776	Intermediate Similarity	NPD3506	Approved
0.776	Intermediate Similarity	NPD7948	Phase 1
0.775	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2172	Phase 1
0.7722	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8094	Discontinued
0.7692	Intermediate Similarity	NPD5017	Discontinued
0.7684	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD4181	Approved
0.765	Intermediate Similarity	NPD4128	Approved
0.7647	Intermediate Similarity	NPD1722	Approved
0.7644	Intermediate Similarity	NPD6665	Discontinued
0.7641	Intermediate Similarity	NPD484	Approved
0.7626	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6999	Discontinued
0.759	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3100	Discontinued
0.7576	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2639	Approved
0.7569	Intermediate Similarity	NPD2642	Approved
0.7566	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8386	Phase 2
0.7514	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD5901	Discontinued
0.7486	Intermediate Similarity	NPD1326	Approved
0.7486	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1325	Approved
0.7464	Intermediate Similarity	NPD7717	Approved
0.7464	Intermediate Similarity	NPD7716	Approved
0.7463	Intermediate Similarity	NPD7665	Phase 2
0.7463	Intermediate Similarity	NPD7666	Phase 3
0.7459	Intermediate Similarity	NPD5140	Approved
0.7459	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5138	Approved
0.745	Intermediate Similarity	NPD7001	Phase 3
0.7432	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD8256	Approved
0.7427	Intermediate Similarity	NPD8257	Approved
0.7427	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD8115	Approved
0.74	Intermediate Similarity	NPD8114	Approved
0.7396	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4600	Approved
0.7374	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4601	Approved
0.7368	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3323	Discontinued
0.7363	Intermediate Similarity	NPD3583	Phase 2
0.7351	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1403	Approved
0.7348	Intermediate Similarity	NPD1404	Approved
0.7345	Intermediate Similarity	NPD4462	Approved
0.7345	Intermediate Similarity	NPD4463	Approved
0.7343	Intermediate Similarity	NPD5818	Discontinued
0.7337	Intermediate Similarity	NPD2844	Phase 3
0.7337	Intermediate Similarity	NPD4639	Approved
0.7337	Intermediate Similarity	NPD2640	Approved
0.7337	Intermediate Similarity	NPD4638	Approved
0.7337	Intermediate Similarity	NPD2641	Approved
0.7337	Intermediate Similarity	NPD7817	Phase 1
0.7337	Intermediate Similarity	NPD4640	Approved
0.7333	Intermediate Similarity	NPD1038	Approved
0.7333	Intermediate Similarity	NPD802	Phase 2
0.733	Intermediate Similarity	NPD4703	Approved
0.733	Intermediate Similarity	NPD4702	Approved
0.7326	Intermediate Similarity	NPD6044	Discontinued
0.731	Intermediate Similarity	NPD2880	Discontinued
0.7308	Intermediate Similarity	NPD8026	Phase 1
0.7308	Intermediate Similarity	NPD6771	Discontinued
0.7292	Intermediate Similarity	NPD7026	Phase 2
0.7292	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD2509	Approved
0.7291	Intermediate Similarity	NPD2510	Approved
0.7286	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6165	Phase 2
0.7277	Intermediate Similarity	NPD7564	Discontinued
0.7277	Intermediate Similarity	NPD6178	Phase 3
0.7277	Intermediate Similarity	NPD6164	Phase 2
0.7268	Intermediate Similarity	NPD4499	Approved
0.7263	Intermediate Similarity	NPD3178	Discontinued
0.7263	Intermediate Similarity	NPD2837	Discontinued
0.7253	Intermediate Similarity	NPD2511	Approved
0.7249	Intermediate Similarity	NPD6368	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8169	Discontinued
0.7225	Intermediate Similarity	NPD5105	Approved
0.7225	Intermediate Similarity	NPD5106	Approved
0.7214	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3717	Discontinued
0.7196	Intermediate Similarity	NPD7865	Approved
0.7194	Intermediate Similarity	NPD3404	Approved
0.7194	Intermediate Similarity	NPD4922	Phase 2
0.7192	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1096	Discontinued
0.7182	Intermediate Similarity	NPD2580	Discontinued
0.7178	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD3609	Approved
0.7166	Intermediate Similarity	NPD3610	Approved
0.7164	Intermediate Similarity	NPD7727	Phase 2
0.7157	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4852	Phase 2
0.715	Intermediate Similarity	NPD5555	Phase 1
0.715	Intermediate Similarity	NPD7308	Discontinued
0.715	Intermediate Similarity	NPD8289	Discontinued
0.7143	Intermediate Similarity	NPD1592	Phase 3
0.7143	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6850	Phase 2
0.7136	Intermediate Similarity	NPD6849	Phase 2
0.7136	Intermediate Similarity	NPD6173	Approved
0.7128	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2442	Approved
0.7122	Intermediate Similarity	NPD2443	Approved
0.7121	Intermediate Similarity	NPD4427	Phase 2
0.712	Intermediate Similarity	NPD6452	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