NPASS Compound

Structure

NPC248283 OpenBabel07101719252D 37 40 0 0 1 0 0 0 0 0999 V2000 0.2588 4.6980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4533 3.2285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0050 2.1766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7121 2.2626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4873 3.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0391 1.9177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7121 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0050 1.5555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7802 2.7802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3320 2.6248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6780 1.7283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3320 1.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9709 4.3672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0391 1.8143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3660 1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9368 2.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2297 3.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 3.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 1.3660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 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 -7.9028 2.9530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 3.9392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 3.9392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 -0.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 -0.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2638 3.6601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 13 22 1 0 0 0 0 14 31 1 0 0 0 0 15 18 1 0 0 0 0 16 23 1 0 0 0 0 16 37 1 0 0 0 0 17 1 1 1 0 0 0 17 24 1 0 0 0 0 17 28 1 0 0 0 0 19 11 1 1 0 0 0 19 25 1 0 0 0 0 19 29 1 0 0 0 0 20 15 1 1 0 0 0 20 27 1 0 0 0 0 20 30 1 0 0 0 0 21 12 1 6 0 0 0 21 26 1 0 0 0 0 21 31 1 0 0 0 0 22 32 2 0 0 0 0 23 22 1 6 0 0 0 23 37 1 0 0 0 0 24 30 2 3 0 0 0 24 33 1 0 0 0 0 25 28 2 3 0 0 0 25 34 1 0 0 0 0 26 29 2 3 0 0 0 26 35 1 0 0 0 0 27 31 1 0 0 0 0 27 36 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.26
Volume:	516.959
LogP:	1.438
LogD:	1.283
LogS:	-2.932
# Rotatable Bonds:	9
TPSA:	137.21
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	4.474
Fsp3:	0.593
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.401
MDCK Permeability:	3.6156194255454466e-05
Pgp-inhibitor:	0.941
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.603
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	61.49839782714844%
Volume Distribution (VD):	0.397
Pgp-substrate:	34.0813102722168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.123
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.46
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	3.568
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.624
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.182
Rat Oral Acute Toxicity:	0.986
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.191
Carcinogencity:	0.338
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC248283

Natural Product ID:	NPC248283
*Common Name:**	QMNUPNOLDLHVTB-IWDBHXEASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QMNUPNOLDLHVTB-IWDBHXEASA-N
Standard InCHI:	InChI=1S/C27H36N4O6/c1-17-24(33)30-20(15-18-9-4-2-5-10-18)27(36)31-14-8-12-21(31)26(35)29-19(25(34)28-17)11-6-3-7-13-22(32)23-16-37-23/h2,4-5,9-10,17,19-21,23H,3,6-8,11-16H2,1H3,(H,28,34)(H,29,35)(H,30,33)/t17-,19-,20-,21+,23-/m0/s1
SMILES:	C[C@H]1C(=N[C@@H](Cc2ccccc2)C(=O)N2CCC[C@@H]2C(=N[C@@H](CCCCCC(=O)[C@@H]2CO2)C(=N1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3315350
PubChem CID:	n.a.
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
NPO32909	tolypocladium sp.	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24999749]

☑ 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
GI50	3
IC50	1
Others	12

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	9
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	46.0	%	PMID[473237]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	19.4	%	PMID[473237]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	34.6	%	PMID[473237]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	19.6	%	PMID[473237]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	45.4	%	PMID[473237]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	35.0	%	PMID[473237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	5.3	nM	PMID[473237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	8.8	nM	PMID[473237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	22.0	nM	PMID[473237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	14.0	nM	PMID[473237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	50.0	nM	PMID[473237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	>	10000.0	nM	PMID[473237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2.0	nM	PMID[473237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	660.0	nM	PMID[473237]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	6.4	nM	PMID[473237]

☑ 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 NPC248283 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	132
0.1-0.2	765
0.2-0.3	3973
0.3-0.4	18730
0.4-0.5	15866
0.5-0.6	2424
0.6-0.7	528
0.7-0.8	227
0.8-0.85	37
0.85-0.9	14
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8806	High Similarity	NPC471264
0.8806	High Similarity	NPC471265
0.875	High Similarity	NPC6975
0.8741	High Similarity	NPC92784
0.8741	High Similarity	NPC476133
0.8741	High Similarity	NPC98424
0.8741	High Similarity	NPC470884
0.8741	High Similarity	NPC178662
0.8696	High Similarity	NPC5620
0.8696	High Similarity	NPC209509
0.8672	High Similarity	NPC252878
0.8661	High Similarity	NPC200964
0.8613	High Similarity	NPC269398
0.8613	High Similarity	NPC263493
0.8605	High Similarity	NPC46427
0.8594	High Similarity	NPC202521
0.8582	High Similarity	NPC287401
0.8516	High Similarity	NPC476990
0.8462	Intermediate Similarity	NPC162104
0.8451	Intermediate Similarity	NPC129666
0.8357	Intermediate Similarity	NPC476978
0.8321	Intermediate Similarity	NPC474082
0.8321	Intermediate Similarity	NPC175726
0.831	Intermediate Similarity	NPC145113
0.8296	Intermediate Similarity	NPC255447
0.8296	Intermediate Similarity	NPC130309
0.8273	Intermediate Similarity	NPC307357
0.8273	Intermediate Similarity	NPC46098
0.8273	Intermediate Similarity	NPC268841
0.8252	Intermediate Similarity	NPC471820
0.8252	Intermediate Similarity	NPC471821
0.8209	Intermediate Similarity	NPC319766
0.8203	Intermediate Similarity	NPC315276
0.8203	Intermediate Similarity	NPC14672
0.8203	Intermediate Similarity	NPC285926
0.8182	Intermediate Similarity	NPC225648
0.8182	Intermediate Similarity	NPC329761
0.8156	Intermediate Similarity	NPC161069
0.8156	Intermediate Similarity	NPC139326
0.8148	Intermediate Similarity	NPC473322
0.814	Intermediate Similarity	NPC470545
0.8129	Intermediate Similarity	NPC68865
0.8125	Intermediate Similarity	NPC240848
0.8099	Intermediate Similarity	NPC315283
0.8099	Intermediate Similarity	NPC52748
0.8099	Intermediate Similarity	NPC314388
0.8088	Intermediate Similarity	NPC200589
0.8077	Intermediate Similarity	NPC470546
0.8069	Intermediate Similarity	NPC2501
0.8062	Intermediate Similarity	NPC470544
0.8054	Intermediate Similarity	NPC197743
0.8054	Intermediate Similarity	NPC297145
0.8047	Intermediate Similarity	NPC33742
0.8042	Intermediate Similarity	NPC316008
0.8042	Intermediate Similarity	NPC313867
0.8015	Intermediate Similarity	NPC111428
0.7986	Intermediate Similarity	NPC314358
0.7986	Intermediate Similarity	NPC262077
0.7969	Intermediate Similarity	NPC276949
0.7969	Intermediate Similarity	NPC35850
0.7956	Intermediate Similarity	NPC300315
0.7931	Intermediate Similarity	NPC138775
0.7926	Intermediate Similarity	NPC101719
0.7917	Intermediate Similarity	NPC315266
0.7905	Intermediate Similarity	NPC122590
0.7902	Intermediate Similarity	NPC176226
0.7887	Intermediate Similarity	NPC476259
0.7887	Intermediate Similarity	NPC163392
0.7887	Intermediate Similarity	NPC239762
0.7877	Intermediate Similarity	NPC105717
0.7852	Intermediate Similarity	NPC222466
0.7823	Intermediate Similarity	NPC283783
0.7778	Intermediate Similarity	NPC197682
0.7708	Intermediate Similarity	NPC469427
0.7708	Intermediate Similarity	NPC469426
0.7708	Intermediate Similarity	NPC168113
0.7687	Intermediate Similarity	NPC16188
0.7671	Intermediate Similarity	NPC471680
0.7671	Intermediate Similarity	NPC322878
0.7667	Intermediate Similarity	NPC286551
0.7652	Intermediate Similarity	NPC239357
0.7651	Intermediate Similarity	NPC7817
0.7651	Intermediate Similarity	NPC475168
0.763	Intermediate Similarity	NPC71684
0.7622	Intermediate Similarity	NPC127741
0.7606	Intermediate Similarity	NPC141050
0.7594	Intermediate Similarity	NPC169328
0.7537	Intermediate Similarity	NPC310467
0.7533	Intermediate Similarity	NPC473491
0.75	Intermediate Similarity	NPC469666
0.75	Intermediate Similarity	NPC470902
0.7482	Intermediate Similarity	NPC136453
0.7465	Intermediate Similarity	NPC246079
0.7464	Intermediate Similarity	NPC22746
0.745	Intermediate Similarity	NPC135121
0.7448	Intermediate Similarity	NPC313694
0.7448	Intermediate Similarity	NPC242159
0.7448	Intermediate Similarity	NPC89489
0.7436	Intermediate Similarity	NPC73655
0.7434	Intermediate Similarity	NPC262166
0.7434	Intermediate Similarity	NPC202198
0.7432	Intermediate Similarity	NPC201244
0.7432	Intermediate Similarity	NPC477217
0.7429	Intermediate Similarity	NPC71933
0.7429	Intermediate Similarity	NPC105114
0.7429	Intermediate Similarity	NPC89923
0.7429	Intermediate Similarity	NPC239990
0.7429	Intermediate Similarity	NPC152850
0.7426	Intermediate Similarity	NPC478015
0.7426	Intermediate Similarity	NPC478014
0.7426	Intermediate Similarity	NPC478016
0.7423	Intermediate Similarity	NPC475421
0.7347	Intermediate Similarity	NPC476989
0.7338	Intermediate Similarity	NPC244509
0.7329	Intermediate Similarity	NPC132636
0.732	Intermediate Similarity	NPC473341
0.731	Intermediate Similarity	NPC9687
0.731	Intermediate Similarity	NPC475598
0.731	Intermediate Similarity	NPC90194
0.731	Intermediate Similarity	NPC151706
0.731	Intermediate Similarity	NPC474811
0.731	Intermediate Similarity	NPC79465
0.731	Intermediate Similarity	NPC118099
0.731	Intermediate Similarity	NPC476102
0.731	Intermediate Similarity	NPC474855
0.731	Intermediate Similarity	NPC475318
0.731	Intermediate Similarity	NPC76785
0.731	Intermediate Similarity	NPC260045
0.731	Intermediate Similarity	NPC49577
0.731	Intermediate Similarity	NPC293377
0.731	Intermediate Similarity	NPC474787
0.731	Intermediate Similarity	NPC273907
0.7308	Intermediate Similarity	NPC469898
0.7297	Intermediate Similarity	NPC77905
0.7289	Intermediate Similarity	NPC470112
0.7289	Intermediate Similarity	NPC167763
0.7289	Intermediate Similarity	NPC470903
0.7279	Intermediate Similarity	NPC237420
0.7273	Intermediate Similarity	NPC157311
0.7267	Intermediate Similarity	NPC196091
0.7261	Intermediate Similarity	NPC469901
0.7255	Intermediate Similarity	NPC233702
0.7244	Intermediate Similarity	NPC324850
0.7239	Intermediate Similarity	NPC317362
0.7239	Intermediate Similarity	NPC136797
0.7239	Intermediate Similarity	NPC318930
0.7239	Intermediate Similarity	NPC317725
0.7239	Intermediate Similarity	NPC326407
0.7226	Intermediate Similarity	NPC476268
0.7226	Intermediate Similarity	NPC469903
0.7222	Intermediate Similarity	NPC44805
0.7222	Intermediate Similarity	NPC8761
0.7219	Intermediate Similarity	NPC311658
0.7218	Intermediate Similarity	NPC474584
0.7208	Intermediate Similarity	NPC56685
0.7208	Intermediate Similarity	NPC261934
0.7208	Intermediate Similarity	NPC5194
0.7202	Intermediate Similarity	NPC299806
0.7197	Intermediate Similarity	NPC244336
0.7185	Intermediate Similarity	NPC188010
0.7178	Intermediate Similarity	NPC137627
0.7174	Intermediate Similarity	NPC477061
0.7174	Intermediate Similarity	NPC80150
0.7174	Intermediate Similarity	NPC45777
0.717	Intermediate Similarity	NPC471051
0.717	Intermediate Similarity	NPC471053
0.717	Intermediate Similarity	NPC471052
0.7152	Intermediate Similarity	NPC81026
0.7143	Intermediate Similarity	NPC473502
0.7134	Intermediate Similarity	NPC26108
0.7134	Intermediate Similarity	NPC477462
0.7132	Intermediate Similarity	NPC224610
0.7132	Intermediate Similarity	NPC113326
0.7132	Intermediate Similarity	NPC194390
0.7132	Intermediate Similarity	NPC88267
0.7117	Intermediate Similarity	NPC89831
0.7107	Intermediate Similarity	NPC241794
0.7099	Intermediate Similarity	NPC280022
0.7089	Intermediate Similarity	NPC1390
0.7089	Intermediate Similarity	NPC62104
0.7086	Intermediate Similarity	NPC266741
0.7081	Intermediate Similarity	NPC254700
0.7078	Intermediate Similarity	NPC324081
0.7067	Intermediate Similarity	NPC251439
0.7055	Intermediate Similarity	NPC233910
0.7055	Intermediate Similarity	NPC245836
0.7055	Intermediate Similarity	NPC475204
0.7055	Intermediate Similarity	NPC475123
0.7054	Intermediate Similarity	NPC471317
0.7051	Intermediate Similarity	NPC473002
0.7051	Intermediate Similarity	NPC39431
0.705	Intermediate Similarity	NPC190663
0.705	Intermediate Similarity	NPC27833
0.7044	Intermediate Similarity	NPC471527
0.7044	Intermediate Similarity	NPC469902
0.7044	Intermediate Similarity	NPC473003
0.7042	Intermediate Similarity	NPC47667
0.7037	Intermediate Similarity	NPC302597
0.7032	Intermediate Similarity	NPC300443
0.7029	Intermediate Similarity	NPC220698

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 NPC248283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	101
0.1-0.2	345
0.2-0.3	722
0.3-0.4	2305
0.4-0.5	3902
0.5-0.6	1430
0.6-0.7	297
0.7-0.8	44
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9921	High Similarity	NPD7113	Clinical (unspecified phase)
0.8947	High Similarity	NPD8172	Phase 2
0.8947	High Similarity	NPD8173	Phase 2
0.8321	Intermediate Similarity	NPD2584	Suspended
0.8074	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD8265	Approved
0.7857	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7613	Discontinued
0.7826	Intermediate Similarity	NPD4125	Approved
0.7754	Intermediate Similarity	NPD4175	Approved
0.7754	Intermediate Similarity	NPD4177	Approved
0.7687	Intermediate Similarity	NPD8323	Discontinued
0.7647	Intermediate Similarity	NPD3072	Approved
0.7647	Intermediate Similarity	NPD3073	Approved
0.7647	Intermediate Similarity	NPD3071	Approved
0.7606	Intermediate Similarity	NPD8416	Discontinued
0.7589	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4761	Approved
0.7574	Intermediate Similarity	NPD4762	Approved
0.7517	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3626	Phase 3
0.75	Intermediate Similarity	NPD6073	Approved
0.75	Intermediate Similarity	NPD5725	Approved
0.7483	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3588	Discontinued
0.7403	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4794	Discontinued
0.7351	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6901	Phase 3
0.7324	Intermediate Similarity	NPD4676	Approved
0.7324	Intermediate Similarity	NPD5263	Approved
0.7324	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8643	Discontinued
0.7292	Intermediate Similarity	NPD5747	Discontinued
0.7292	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4153	Approved
0.7211	Intermediate Similarity	NPD6852	Discontinued
0.7183	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8076	Discontinued
0.7179	Intermediate Similarity	NPD8417	Discontinued
0.7163	Intermediate Similarity	NPD6792	Phase 3
0.7153	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6676	Phase 2
0.7133	Intermediate Similarity	NPD2436	Approved
0.7133	Intermediate Similarity	NPD2437	Approved
0.7133	Intermediate Similarity	NPD3040	Approved
0.7123	Intermediate Similarity	NPD6623	Phase 3
0.7103	Intermediate Similarity	NPD1330	Phase 2
0.7103	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5264	Approved
0.7086	Intermediate Similarity	NPD5265	Approved
0.7075	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7964	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7965	Phase 2
0.7067	Intermediate Similarity	NPD7720	Phase 2
0.7067	Intermediate Similarity	NPD4152	Approved
0.7067	Intermediate Similarity	NPD2022	Approved
0.7059	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2574	Discontinued
0.7055	Intermediate Similarity	NPD2566	Approved
0.7055	Intermediate Similarity	NPD2570	Approved
0.7055	Intermediate Similarity	NPD3087	Approved
0.7055	Intermediate Similarity	NPD3090	Approved
0.7055	Intermediate Similarity	NPD2573	Approved
0.7055	Intermediate Similarity	NPD3615	Approved
0.7055	Intermediate Similarity	NPD3089	Approved
0.7055	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3616	Approved
0.7055	Intermediate Similarity	NPD4745	Approved
0.7055	Intermediate Similarity	NPD3088	Approved
0.7055	Intermediate Similarity	NPD2571	Approved
0.7055	Intermediate Similarity	NPD4746	Phase 3
0.7055	Intermediate Similarity	NPD3614	Approved
0.7051	Intermediate Similarity	NPD8315	Phase 1
0.7042	Intermediate Similarity	NPD3125	Approved
0.7034	Intermediate Similarity	NPD2046	Approved
0.7034	Intermediate Similarity	NPD2047	Approved
0.7034	Intermediate Similarity	NPD2051	Approved
0.7034	Intermediate Similarity	NPD21	Approved
0.7034	Intermediate Similarity	NPD2044	Approved
0.7034	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2048	Approved
0.7034	Intermediate Similarity	NPD2045	Approved
0.7034	Intermediate Similarity	NPD2043	Approved
0.702	Intermediate Similarity	NPD6681	Discovery
0.7014	Intermediate Similarity	NPD5759	Approved
0.7007	Intermediate Similarity	NPD5296	Approved
0.7007	Intermediate Similarity	NPD5323	Approved
0.7	Intermediate Similarity	NPD7512	Approved
0.7	Intermediate Similarity	NPD7511	Approved
0.6986	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7011	Discontinued
0.698	Remote Similarity	NPD4126	Approved
0.6978	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4677	Discontinued
0.697	Remote Similarity	NPD8124	Phase 3
0.697	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2613	Approved
0.6959	Remote Similarity	NPD4685	Phase 3
0.6959	Remote Similarity	NPD4684	Phase 3
0.6959	Remote Similarity	NPD4686	Approved
0.6954	Remote Similarity	NPD2087	Approved
0.6954	Remote Similarity	NPD2088	Approved
0.695	Remote Similarity	NPD2611	Approved
0.695	Remote Similarity	NPD2610	Approved
0.695	Remote Similarity	NPD3131	Approved
0.695	Remote Similarity	NPD4217	Approved
0.695	Remote Similarity	NPD3132	Approved
0.695	Remote Similarity	NPD2609	Approved
0.695	Remote Similarity	NPD2608	Approved
0.695	Remote Similarity	NPD4218	Approved
0.695	Remote Similarity	NPD2612	Approved
0.695	Remote Similarity	NPD4216	Approved
0.695	Remote Similarity	NPD4215	Approved
0.6939	Remote Similarity	NPD941	Approved
0.6939	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1348	Approved
0.6933	Remote Similarity	NPD3480	Approved
0.6929	Remote Similarity	NPD7342	Discontinued
0.6918	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2218	Phase 2
0.6906	Remote Similarity	NPD6343	Approved
0.6906	Remote Similarity	NPD6345	Approved
0.6906	Remote Similarity	NPD2217	Approved
0.6903	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3282	Phase 1
0.6903	Remote Similarity	NPD3283	Phase 3
0.6903	Remote Similarity	NPD6088	Approved
0.6894	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7130	Phase 3
0.6884	Remote Similarity	NPD3123	Discovery
0.6883	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7131	Phase 3
0.6871	Remote Similarity	NPD4621	Approved
0.6871	Remote Similarity	NPD4619	Approved
0.6871	Remote Similarity	NPD5299	Approved
0.6867	Remote Similarity	NPD6294	Approved
0.6867	Remote Similarity	NPD6295	Approved
0.6838	Remote Similarity	NPD480	Approved
0.6835	Remote Similarity	NPD4646	Approved
0.6835	Remote Similarity	NPD4648	Approved
0.6835	Remote Similarity	NPD4647	Approved
0.6832	Remote Similarity	NPD4557	Approved
0.6828	Remote Similarity	NPD4151	Approved
0.6818	Remote Similarity	NPD2575	Approved
0.6818	Remote Similarity	NPD999	Phase 2
0.6815	Remote Similarity	NPD5230	Approved
0.6815	Remote Similarity	NPD5229	Approved
0.6815	Remote Similarity	NPD3644	Approved
0.6815	Remote Similarity	NPD3642	Approved
0.6815	Remote Similarity	NPD3643	Approved
0.6815	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2031	Discontinued
0.6806	Remote Similarity	NPD6325	Discontinued
0.6806	Remote Similarity	NPD5367	Discontinued
0.6803	Remote Similarity	NPD4738	Phase 2
0.68	Remote Similarity	NPD7510	Approved
0.6795	Remote Similarity	NPD5614	Approved
0.6795	Remote Similarity	NPD5613	Approved
0.6795	Remote Similarity	NPD3987	Approved
0.6795	Remote Similarity	NPD3988	Approved
0.6788	Remote Similarity	NPD7485	Phase 3
0.6788	Remote Similarity	NPD7484	Phase 3
0.6783	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8303	Discontinued
0.6759	Remote Similarity	NPD2625	Approved
0.6759	Remote Similarity	NPD2626	Approved
0.6759	Remote Similarity	NPD2628	Approved
0.6759	Remote Similarity	NPD2627	Approved
0.6759	Remote Similarity	NPD2160	Approved
0.6759	Remote Similarity	NPD2159	Approved
0.6757	Remote Similarity	NPD5581	Approved
0.6748	Remote Similarity	NPD8351	Phase 2
0.6739	Remote Similarity	NPD1711	Phase 2
0.6733	Remote Similarity	NPD3577	Discontinued
0.6733	Remote Similarity	NPD3908	Approved
0.6728	Remote Similarity	NPD7599	Phase 2
0.672	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7522	Discontinued
0.6711	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7508	Discontinued
0.6687	Remote Similarity	NPD7600	Phase 2
0.6685	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD998	Approved
0.6667	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3598	Phase 3
0.6629	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5981	Approved
0.6618	Remote Similarity	NPD3581	Discontinued
0.6604	Remote Similarity	NPD3822	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data