NPASS Compound

Structure

CID124549 OpenBabel06191715482D 50 51 0 0 1 0 0 0 0 0999 V2000 0.6492 -1.2210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1673 0.2332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1262 -1.1510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7090 6.6983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4325 6.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5844 -2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8562 -2.2019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3591 0.7980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8170 3.6427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3373 5.9390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0760 -1.6286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5097 -0.7115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7903 6.4164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0114 5.7892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6366 7.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2930 3.6701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4840 4.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1651 4.8011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4829 8.3926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9840 2.7191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2471 -0.1584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6203 6.2866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7533 -1.7603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4987 0.2885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8767 3.3024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6750 3.6701 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3862 4.1739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4479 0.4427 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7193 5.2915 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8194 -0.7625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6272 0.7789 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0575 2.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0739 4.4693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7235 -0.2466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9675 1.7192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7171 5.2254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 -0.5330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3291 9.3807 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.9093 1.3299 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7541 5.0300 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8145 -0.6634 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9840 2.7191 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0574 2.3354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7633 5.1937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2842 -1.0746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9510 1.5383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9465 6.1987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4596 -1.4553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6394 4.8389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 23 1 0 0 0 0 10 40 1 0 0 0 0 11 41 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 19 3 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 19 38 1 0 0 0 0 20 42 1 0 0 0 0 24 8 1 1 0 0 0 25 9 1 1 0 0 0 25 27 1 0 0 0 0 25 32 1 0 0 0 0 26 17 1 6 0 0 0 26 33 1 0 0 0 0 26 42 1 0 0 0 0 27 18 1 1 0 0 0 27 49 1 0 0 0 0 28 21 1 6 0 0 0 28 34 1 0 0 0 0 28 39 1 0 0 0 0 29 22 1 6 0 0 0 29 36 1 0 0 0 0 29 40 1 0 0 0 0 30 23 1 6 0 0 0 30 37 1 0 0 0 0 30 41 1 0 0 0 0 31 24 1 6 0 0 0 31 35 1 0 0 0 0 31 50 1 0 0 0 0 32 39 2 3 0 0 0 32 43 1 0 0 0 0 33 40 1 0 0 0 0 33 44 2 0 0 0 0 34 41 1 0 0 0 0 34 45 2 0 0 0 0 35 42 1 0 0 0 0 35 46 2 0 0 0 0 36 47 2 0 0 0 0 36 49 1 0 0 0 0 37 48 2 0 0 0 0 37 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	766.35
Volume:	743.896
LogP:	4.616
LogD:	3.077
LogS:	-4.385
# Rotatable Bonds:	8
TPSA:	142.63
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.221
Synthetic Accessibility Score:	5.708
Fsp3:	0.784
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:	-5.11
MDCK Permeability:	1.5907571651041508e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.78
20% Bioavailability (F20%):	0.861
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	94.48377227783203%
Volume Distribution (VD):	1.498
Pgp-substrate:	0.7994406819343567%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.706
CYP2C19-substrate:	0.779
CYP2C9-inhibitor:	0.335
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.285
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.851

ADMET: Excretion

Clearance (CL):	3.788
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.994
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.168
Carcinogencity:	0.481
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.593

Download Data

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

Natural Product: NPC124549

Natural Product ID:	NPC124549
*Common Name:**	Veraguamide A
IUPAC Name:	(3S,6S,9S,12S,13R,16S,19S)-13-(5-bromopent-4-ynyl)-3-[(2S)-butan-2-yl]-7,12,17-trimethyl-6,9,16-tri(propan-2-yl)-4,14-dioxa-1,7,10,17-tetrazabicyclo[17.3.0]docosane-2,5,8,11,15,18-hexone
Synonyms:	Veraguamide A
Standard InCHIKey:	WWYBIFCBAWCPFI-AVCHBABLSA-N
Standard InCHI:	InChI=1S/C37H59BrN4O8/c1-12-24(8)31-35(46)42-20-16-17-26(42)33(44)40(10)29(22(4)5)36(47)49-27(18-14-13-15-19-38)25(9)32(43)39-28(21(2)3)34(45)41(11)30(23(6)7)37(48)50-31/h21-31H,12-14,16-18,20H2,1-11H3,(H,39,43)/t24-,25-,26-,27+,28-,29-,30-,31-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=O)N(C)[C@@H](C(C)C)C(=O)O[C@H](CCCC#CBr)[C@H](C)C(=N[C@@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1783105
PubChem CID:	53355336
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11975485]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350149]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21446699]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21488639]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	Isla Canales de Afuera on the Pacific coast of Panama (741.617'N, 8138.379'E)	n.a.	PMID[21488639]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21751786]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28006911]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28202328]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31763840]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9748368]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1614	Silene baccifera	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27391	Ammopiptanthus mongolicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12359	Rhodotorula toruloides	Species	Sporidiobolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1614	Silene baccifera	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16825	Scabiosa columbaria	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20342	Lichtheimia corymbifera	Species	Lichtheimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16336	Magnolia tomentosa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29477	Hymenopellis radicata	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25587	Pearsonia sessilifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16059	Lobelia polyphylla	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27391	Ammopiptanthus mongolicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2278	Serenoa serrulata	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18009	Cicer flexuosum	Species	Fabaceae	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	2
LD50	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	26000.0	nM	PMID[557464]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	21000.0	nM	PMID[557464]
NPT397	Cell Line	NCI-H460	Homo sapiens	LD50	=	141.0	nM	PMID[557465]

☑ 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 NPC124549 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	176
0.1-0.2	6870
0.2-0.3	20300
0.3-0.4	13062
0.4-0.5	1716
0.5-0.6	362
0.6-0.7	165
0.7-0.8	30
0.8-0.85	6
0.85-0.9	2
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC198344
0.9588	High Similarity	NPC5864
0.9588	High Similarity	NPC124554
0.9588	High Similarity	NPC301148
0.9278	High Similarity	NPC220234
0.9118	High Similarity	NPC67009
0.8571	High Similarity	NPC171734
0.8462	Intermediate Similarity	NPC323720
0.81	Intermediate Similarity	NPC62263
0.81	Intermediate Similarity	NPC173763
0.81	Intermediate Similarity	NPC471098
0.8	Intermediate Similarity	NPC474576
0.79	Intermediate Similarity	NPC474593
0.79	Intermediate Similarity	NPC475801
0.7642	Intermediate Similarity	NPC475440
0.7387	Intermediate Similarity	NPC475637
0.7308	Intermediate Similarity	NPC476019
0.7273	Intermediate Similarity	NPC471097
0.7273	Intermediate Similarity	NPC475149
0.7216	Intermediate Similarity	NPC473741
0.7216	Intermediate Similarity	NPC477145
0.713	Intermediate Similarity	NPC134504
0.713	Intermediate Similarity	NPC47076
0.7129	Intermediate Similarity	NPC472351
0.7115	Intermediate Similarity	NPC322966
0.71	Intermediate Similarity	NPC246005
0.7091	Intermediate Similarity	NPC475791
0.7091	Intermediate Similarity	NPC13175
0.7075	Intermediate Similarity	NPC315237
0.7	Intermediate Similarity	NPC475758
0.6981	Remote Similarity	NPC477538
0.6979	Remote Similarity	NPC178919
0.6979	Remote Similarity	NPC263281
0.6972	Remote Similarity	NPC473597
0.6967	Remote Similarity	NPC477238
0.6949	Remote Similarity	NPC471202
0.6949	Remote Similarity	NPC63191
0.6931	Remote Similarity	NPC53858
0.6931	Remote Similarity	NPC84128
0.6907	Remote Similarity	NPC86064
0.6832	Remote Similarity	NPC476302
0.6832	Remote Similarity	NPC23984
0.6804	Remote Similarity	NPC43219
0.6803	Remote Similarity	NPC477237
0.678	Remote Similarity	NPC476875
0.6739	Remote Similarity	NPC329761
0.6739	Remote Similarity	NPC225648
0.6733	Remote Similarity	NPC476117
0.6733	Remote Similarity	NPC476243
0.6733	Remote Similarity	NPC476137
0.6733	Remote Similarity	NPC476156
0.6667	Remote Similarity	NPC478256
0.6638	Remote Similarity	NPC241394
0.6634	Remote Similarity	NPC31756
0.6612	Remote Similarity	NPC472536
0.6612	Remote Similarity	NPC103391
0.6571	Remote Similarity	NPC227051
0.6562	Remote Similarity	NPC29598
0.6562	Remote Similarity	NPC212866
0.6552	Remote Similarity	NPC128303
0.6538	Remote Similarity	NPC235078
0.6525	Remote Similarity	NPC129666
0.648	Remote Similarity	NPC470652
0.6476	Remote Similarity	NPC155670
0.6476	Remote Similarity	NPC95478
0.6476	Remote Similarity	NPC145748
0.6466	Remote Similarity	NPC476877
0.6458	Remote Similarity	NPC10716
0.6429	Remote Similarity	NPC315188
0.6422	Remote Similarity	NPC477729
0.6406	Remote Similarity	NPC470654
0.6406	Remote Similarity	NPC470650
0.6406	Remote Similarity	NPC470653
0.6377	Remote Similarity	NPC263493
0.6377	Remote Similarity	NPC269398
0.6357	Remote Similarity	NPC309525
0.6357	Remote Similarity	NPC5620
0.6356	Remote Similarity	NPC476876
0.6355	Remote Similarity	NPC477539
0.6346	Remote Similarity	NPC470783
0.6331	Remote Similarity	NPC139326
0.633	Remote Similarity	NPC275715
0.6311	Remote Similarity	NPC315535
0.6311	Remote Similarity	NPC478017
0.6311	Remote Similarity	NPC315131
0.629	Remote Similarity	NPC296043
0.6288	Remote Similarity	NPC313657
0.6268	Remote Similarity	NPC138775
0.625	Remote Similarity	NPC207820
0.624	Remote Similarity	NPC329216
0.6214	Remote Similarity	NPC316242
0.6172	Remote Similarity	NPC160688
0.6159	Remote Similarity	NPC471264
0.6159	Remote Similarity	NPC471265
0.6154	Remote Similarity	NPC312315
0.6154	Remote Similarity	NPC145113
0.6147	Remote Similarity	NPC477728
0.6142	Remote Similarity	NPC469899
0.6139	Remote Similarity	NPC266888
0.6139	Remote Similarity	NPC138435
0.6139	Remote Similarity	NPC209156
0.6139	Remote Similarity	NPC256312
0.6139	Remote Similarity	NPC161774
0.6136	Remote Similarity	NPC470651
0.6136	Remote Similarity	NPC470655
0.6134	Remote Similarity	NPC205176
0.6119	Remote Similarity	NPC120335
0.6099	Remote Similarity	NPC161069
0.6078	Remote Similarity	NPC327272
0.6043	Remote Similarity	NPC68865
0.604	Remote Similarity	NPC141325
0.6038	Remote Similarity	NPC475542
0.6019	Remote Similarity	NPC476130
0.6019	Remote Similarity	NPC476324
0.6017	Remote Similarity	NPC188785
0.6014	Remote Similarity	NPC209509
0.6	Remote Similarity	NPC470884
0.6	Remote Similarity	NPC178662
0.6	Remote Similarity	NPC476133
0.6	Remote Similarity	NPC98424
0.6	Remote Similarity	NPC92784
0.6	Remote Similarity	NPC240848
0.6	Remote Similarity	NPC297145
0.6	Remote Similarity	NPC197743
0.5986	Remote Similarity	NPC162104
0.5954	Remote Similarity	NPC50520
0.5944	Remote Similarity	NPC476978
0.5941	Remote Similarity	NPC196007
0.5941	Remote Similarity	NPC214532
0.5941	Remote Similarity	NPC76297
0.5926	Remote Similarity	NPC477730
0.5905	Remote Similarity	NPC233108
0.59	Remote Similarity	NPC473985
0.59	Remote Similarity	NPC474298
0.59	Remote Similarity	NPC475808
0.59	Remote Similarity	NPC28348
0.59	Remote Similarity	NPC474299
0.589	Remote Similarity	NPC471821
0.589	Remote Similarity	NPC471820
0.5878	Remote Similarity	NPC273185
0.585	Remote Similarity	NPC2501
0.5845	Remote Similarity	NPC239762
0.5845	Remote Similarity	NPC163392
0.5826	Remote Similarity	NPC38172
0.581	Remote Similarity	NPC59867
0.5804	Remote Similarity	NPC473495
0.5804	Remote Similarity	NPC52533
0.5789	Remote Similarity	NPC477518
0.5743	Remote Similarity	NPC193280
0.5743	Remote Similarity	NPC314273
0.5734	Remote Similarity	NPC46098
0.5734	Remote Similarity	NPC307357
0.5734	Remote Similarity	NPC268841
0.5733	Remote Similarity	NPC122590
0.5726	Remote Similarity	NPC296143
0.5726	Remote Similarity	NPC117829
0.5704	Remote Similarity	NPC127741
0.5701	Remote Similarity	NPC473984
0.5691	Remote Similarity	NPC471844
0.5688	Remote Similarity	NPC284456
0.5688	Remote Similarity	NPC6902
0.5686	Remote Similarity	NPC476285
0.5686	Remote Similarity	NPC476291
0.5685	Remote Similarity	NPC316008
0.5685	Remote Similarity	NPC313867
0.5676	Remote Similarity	NPC277918
0.5673	Remote Similarity	NPC126186
0.5646	Remote Similarity	NPC314358
0.5641	Remote Similarity	NPC280066
0.5636	Remote Similarity	NPC47135
0.5625	Remote Similarity	NPC469597
0.5616	Remote Similarity	NPC52748
0.5616	Remote Similarity	NPC314388
0.5616	Remote Similarity	NPC315283
0.5614	Remote Similarity	NPC155230
0.5603	Remote Similarity	NPC270005
0.5603	Remote Similarity	NPC208537
0.56	Remote Similarity	NPC15413

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 NPC124549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	91
0.1-0.2	1447
0.2-0.3	4993
0.3-0.4	2005
0.4-0.5	516
0.5-0.6	79
0.6-0.7	19
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.699	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7760	Phase 2
0.6827	Remote Similarity	NPD7759	Phase 2
0.6757	Remote Similarity	NPD3714	Approved
0.6757	Remote Similarity	NPD3715	Approved
0.6757	Remote Similarity	NPD3713	Approved
0.6667	Remote Similarity	NPD7763	Phase 2
0.6667	Remote Similarity	NPD4261	Phase 1
0.6667	Remote Similarity	NPD7762	Phase 2
0.6607	Remote Similarity	NPD8038	Phase 2
0.6577	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7840	Approved
0.6442	Remote Similarity	NPD2683	Discontinued
0.6325	Remote Similarity	NPD6122	Discontinued
0.6311	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3177	Phase 3
0.6216	Remote Similarity	NPD2682	Approved
0.6129	Remote Similarity	NPD8298	Phase 2
0.6018	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2696	Approved
0.6	Remote Similarity	NPD2697	Approved
0.6	Remote Similarity	NPD2695	Approved
0.6	Remote Similarity	NPD2694	Approved
0.5983	Remote Similarity	NPD4825	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD1125	Discovery
0.5952	Remote Similarity	NPD7915	Approved
0.5952	Remote Similarity	NPD7916	Approved
0.5948	Remote Similarity	NPD1784	Approved
0.59	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.59	Remote Similarity	NPD620	Approved
0.5798	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6937	Approved
0.5758	Remote Similarity	NPD7652	Discontinued
0.5755	Remote Similarity	NPD8143	Approved
0.5755	Remote Similarity	NPD8144	Approved
0.5714	Remote Similarity	NPD3176	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.566	Remote Similarity	NPD2689	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4272	Discontinued
0.5636	Remote Similarity	NPD7345	Approved
0.5635	Remote Similarity	NPD4260	Discontinued
0.5625	Remote Similarity	NPD5791	Phase 2

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