NPASS Compound

Structure

NPC14812 OpenBabel07101719512D 42 49 0 0 1 0 0 0 0 0999 V2000 -0.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2332 -5.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3806 -6.0548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6555 -3.8913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9015 -1.5797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9401 0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6086 -2.2868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3523 1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9356 -1.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5334 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3498 -3.2527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3578 1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3667 -5.2116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5577 -4.6238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9767 -2.6707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6768 -2.8045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7857 -3.2584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3839 -3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9890 -2.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9422 -4.2461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5823 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9511 -2.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5933 -3.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3544 -5.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -2.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9299 -4.4026 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4013 -3.6361 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4122 -1.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1701 -1.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1810 -4.3406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9021 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2079 -3.5962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7601 -2.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 29 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 6 42 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 19 2 0 0 0 0 12 21 2 0 0 0 0 13 22 2 0 0 0 0 14 23 2 0 0 0 0 15 16 2 0 0 0 0 15 29 1 0 0 0 0 16 35 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 30 1 0 0 0 0 18 33 1 6 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 20 25 2 0 0 0 0 21 23 1 0 0 0 0 21 31 1 0 0 0 0 22 34 1 0 0 0 0 23 36 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 0 0 0 0 25 29 1 0 0 0 0 25 34 1 0 0 0 0 26 37 1 0 0 0 0 26 38 2 0 0 0 0 27 31 1 6 0 0 0 27 32 1 0 0 0 0 27 42 1 0 0 0 0 28 32 1 0 0 0 0 28 35 1 0 0 0 0 28 39 2 0 0 0 0 30 36 1 0 0 0 0 31 33 1 1 0 0 0 31 40 1 0 0 0 0 32 37 1 0 0 0 0 32 41 1 1 0 0 0 33 36 1 6 0 0 0 33 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.25
Volume:	569.809
LogP:	5.412
LogD:	3.896
LogS:	-5.649
# Rotatable Bonds:	1
TPSA:	109.34
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	5.755
Fsp3:	0.394
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:	-5.269
MDCK Permeability:	2.5759238269529305e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.414
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	96.18020629882812%
Volume Distribution (VD):	2.038
Pgp-substrate:	1.2250264883041382%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.939
CYP2C9-substrate:	0.281
CYP2D6-inhibitor:	0.873
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.974
CYP3A4-substrate:	0.977

ADMET: Excretion

Clearance (CL):	5.344
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.999
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.897
Carcinogencity:	0.98
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.669

Download Data

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

Natural Product: NPC14812

Natural Product ID:	NPC14812
*Common Name:**	Okaramine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PNJDFZNVNWQTFD-KTJJPEJQSA-N
Standard InCHI:	InChI=1S/C33H34N4O5/c1-18-30(4,5)36-23-14-10-8-12-21(23)31(40)27(42-6)32(41)28(39)35-16-15-29(2,3)25-20(19-11-7-9-13-22(19)34-25)17-24(35)26(38)37(32)33(18,31)36/h7-18,27,34,40-41H,1-6H3/b16-15-,24-17-/t18-,27+,31+,32+,33+/m1/s1
SMILES:	CO[C@@H]1[C@]2(O)C(=O)N3C=CC(C)(C)c4c(C=C3C(=O)N2[C@]23[C@]1(O)c1ccccc1N3C([C@H]2C)(C)C)c1ccccc1[nH]4
Synthetic Gene Cluster:	BGC0001717;
ChEMBL Identifier:	CHEMBL501004
PubChem CID:	14312904
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	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
LD50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3978	Organism	Bombyx mori	Bombyx mori	LD50	=	0.2	ug	PMID[496553]
NPT3978	Organism	Bombyx mori	Bombyx mori	LD50	=	0.2	mg.kg-1	PMID[496554]

☑ 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 NPC14812 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	384
0.1-0.2	1810
0.2-0.3	9120
0.3-0.4	21030
0.4-0.5	5310
0.5-0.6	3063
0.6-0.7	1729
0.7-0.8	247
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8869	High Similarity	NPC31097
0.8824	High Similarity	NPC474896
0.8694	High Similarity	NPC272174
0.8043	Intermediate Similarity	NPC475969
0.8043	Intermediate Similarity	NPC474877
0.8043	Intermediate Similarity	NPC477177
0.8043	Intermediate Similarity	NPC475859
0.8	Intermediate Similarity	NPC470729
0.8	Intermediate Similarity	NPC470730
0.8	Intermediate Similarity	NPC477176
0.8	Intermediate Similarity	NPC477175
0.7975	Intermediate Similarity	NPC63279
0.7941	Intermediate Similarity	NPC297642
0.7932	Intermediate Similarity	NPC165743
0.7769	Intermediate Similarity	NPC470785
0.7727	Intermediate Similarity	NPC184680
0.7695	Intermediate Similarity	NPC470784
0.7532	Intermediate Similarity	NPC162860
0.7521	Intermediate Similarity	NPC478157
0.7489	Intermediate Similarity	NPC470732
0.7489	Intermediate Similarity	NPC470731
0.7478	Intermediate Similarity	NPC277350
0.747	Intermediate Similarity	NPC314882
0.7459	Intermediate Similarity	NPC323752
0.7457	Intermediate Similarity	NPC478158
0.7452	Intermediate Similarity	NPC315467
0.7446	Intermediate Similarity	NPC54420
0.7438	Intermediate Similarity	NPC33949
0.7426	Intermediate Similarity	NPC281049
0.7418	Intermediate Similarity	NPC89987
0.7388	Intermediate Similarity	NPC323198
0.7384	Intermediate Similarity	NPC312645
0.7384	Intermediate Similarity	NPC472285
0.7354	Intermediate Similarity	NPC478006
0.7353	Intermediate Similarity	NPC477714
0.7339	Intermediate Similarity	NPC474183
0.7331	Intermediate Similarity	NPC89508
0.7331	Intermediate Similarity	NPC54744
0.7313	Intermediate Similarity	NPC260909
0.7308	Intermediate Similarity	NPC223791
0.7308	Intermediate Similarity	NPC107077
0.7296	Intermediate Similarity	NPC244741
0.729	Intermediate Similarity	NPC478010
0.729	Intermediate Similarity	NPC478009
0.7287	Intermediate Similarity	NPC325976
0.7284	Intermediate Similarity	NPC319232
0.7284	Intermediate Similarity	NPC24370
0.7273	Intermediate Similarity	NPC107836
0.7273	Intermediate Similarity	NPC476817
0.7273	Intermediate Similarity	NPC64216
0.7261	Intermediate Similarity	NPC214428
0.7254	Intermediate Similarity	NPC476491
0.7249	Intermediate Similarity	NPC171317
0.7247	Intermediate Similarity	NPC284888
0.7247	Intermediate Similarity	NPC220852
0.7243	Intermediate Similarity	NPC19170
0.7238	Intermediate Similarity	NPC477715
0.7236	Intermediate Similarity	NPC14288
0.7234	Intermediate Similarity	NPC469743
0.7229	Intermediate Similarity	NPC475506
0.7229	Intermediate Similarity	NPC285343
0.7228	Intermediate Similarity	NPC195788
0.7228	Intermediate Similarity	NPC237901
0.7227	Intermediate Similarity	NPC477979
0.7224	Intermediate Similarity	NPC56109
0.7224	Intermediate Similarity	NPC191382
0.7222	Intermediate Similarity	NPC477109
0.7222	Intermediate Similarity	NPC477108
0.7222	Intermediate Similarity	NPC477107
0.7218	Intermediate Similarity	NPC321939
0.7214	Intermediate Similarity	NPC314056
0.7206	Intermediate Similarity	NPC63031
0.7203	Intermediate Similarity	NPC234999
0.7198	Intermediate Similarity	NPC471436
0.7198	Intermediate Similarity	NPC155143
0.7195	Intermediate Similarity	NPC322135
0.7195	Intermediate Similarity	NPC326363
0.7191	Intermediate Similarity	NPC314176
0.7184	Intermediate Similarity	NPC118559
0.7184	Intermediate Similarity	NPC304307
0.7184	Intermediate Similarity	NPC261251
0.7184	Intermediate Similarity	NPC124920
0.7184	Intermediate Similarity	NPC34580
0.7183	Intermediate Similarity	NPC17487
0.7183	Intermediate Similarity	NPC201831
0.7173	Intermediate Similarity	NPC320968
0.7172	Intermediate Similarity	NPC476818
0.7167	Intermediate Similarity	NPC165599
0.716	Intermediate Similarity	NPC327095
0.716	Intermediate Similarity	NPC253987
0.716	Intermediate Similarity	NPC155444
0.716	Intermediate Similarity	NPC28945
0.716	Intermediate Similarity	NPC312942
0.7155	Intermediate Similarity	NPC471944
0.7154	Intermediate Similarity	NPC478011
0.7154	Intermediate Similarity	NPC478012
0.7154	Intermediate Similarity	NPC297862
0.7154	Intermediate Similarity	NPC100547
0.7143	Intermediate Similarity	NPC475778
0.7143	Intermediate Similarity	NPC214142
0.7143	Intermediate Similarity	NPC75634
0.7132	Intermediate Similarity	NPC478013
0.7131	Intermediate Similarity	NPC82472
0.7131	Intermediate Similarity	NPC475422
0.7131	Intermediate Similarity	NPC40455
0.7126	Intermediate Similarity	NPC95240
0.7126	Intermediate Similarity	NPC223409
0.7125	Intermediate Similarity	NPC204491
0.7125	Intermediate Similarity	NPC203614
0.7114	Intermediate Similarity	NPC475258
0.7102	Intermediate Similarity	NPC141428
0.7101	Intermediate Similarity	NPC82370
0.71	Intermediate Similarity	NPC473640
0.71	Intermediate Similarity	NPC52557
0.7085	Intermediate Similarity	NPC194740
0.7073	Intermediate Similarity	NPC909
0.7073	Intermediate Similarity	NPC475338
0.7071	Intermediate Similarity	NPC87856
0.7071	Intermediate Similarity	NPC151976
0.7069	Intermediate Similarity	NPC241024
0.7068	Intermediate Similarity	NPC321592
0.7068	Intermediate Similarity	NPC54803
0.7066	Intermediate Similarity	NPC303658
0.7066	Intermediate Similarity	NPC473310
0.7064	Intermediate Similarity	NPC473376
0.7063	Intermediate Similarity	NPC478029
0.7061	Intermediate Similarity	NPC475271
0.7056	Intermediate Similarity	NPC69843
0.7054	Intermediate Similarity	NPC36405
0.7054	Intermediate Similarity	NPC181081
0.7054	Intermediate Similarity	NPC132211
0.7054	Intermediate Similarity	NPC133609
0.7048	Intermediate Similarity	NPC175474
0.7046	Intermediate Similarity	NPC258062
0.7046	Intermediate Similarity	NPC127677
0.7046	Intermediate Similarity	NPC87755
0.7043	Intermediate Similarity	NPC289299
0.7043	Intermediate Similarity	NPC57994
0.704	Intermediate Similarity	NPC70155
0.704	Intermediate Similarity	NPC91179
0.7039	Intermediate Similarity	NPC81654
0.7039	Intermediate Similarity	NPC249150
0.7039	Intermediate Similarity	NPC49196
0.7039	Intermediate Similarity	NPC195461
0.7039	Intermediate Similarity	NPC79129
0.7039	Intermediate Similarity	NPC313985
0.7036	Intermediate Similarity	NPC472207
0.7027	Intermediate Similarity	NPC189079
0.7025	Intermediate Similarity	NPC305984
0.7025	Intermediate Similarity	NPC79386
0.7024	Intermediate Similarity	NPC184225
0.7012	Intermediate Similarity	NPC33064
0.7012	Intermediate Similarity	NPC245055
0.7004	Intermediate Similarity	NPC270918
0.7004	Intermediate Similarity	NPC46225
0.7004	Intermediate Similarity	NPC225821
0.6996	Remote Similarity	NPC471198
0.6996	Remote Similarity	NPC174788
0.6996	Remote Similarity	NPC100321
0.6992	Remote Similarity	NPC229893
0.6984	Remote Similarity	NPC57453
0.6984	Remote Similarity	NPC478028
0.6983	Remote Similarity	NPC232130
0.6983	Remote Similarity	NPC141454
0.6979	Remote Similarity	NPC162730
0.6976	Remote Similarity	NPC57690
0.6974	Remote Similarity	NPC213629
0.6966	Remote Similarity	NPC252338
0.6964	Remote Similarity	NPC474196
0.6964	Remote Similarity	NPC235885
0.6957	Remote Similarity	NPC55493
0.6957	Remote Similarity	NPC15801
0.6955	Remote Similarity	NPC125181
0.6955	Remote Similarity	NPC263117
0.6955	Remote Similarity	NPC471197
0.6955	Remote Similarity	NPC242872
0.6953	Remote Similarity	NPC50503
0.6953	Remote Similarity	NPC131887
0.6953	Remote Similarity	NPC470499
0.6947	Remote Similarity	NPC470003
0.6946	Remote Similarity	NPC471951
0.6946	Remote Similarity	NPC477548
0.6946	Remote Similarity	NPC471946
0.6943	Remote Similarity	NPC472112
0.6942	Remote Similarity	NPC474412
0.6939	Remote Similarity	NPC474195
0.6936	Remote Similarity	NPC300183
0.6933	Remote Similarity	NPC473362
0.6933	Remote Similarity	NPC166492
0.6929	Remote Similarity	NPC41679
0.6926	Remote Similarity	NPC475736
0.6923	Remote Similarity	NPC293917
0.6923	Remote Similarity	NPC192674
0.692	Remote Similarity	NPC27324
0.692	Remote Similarity	NPC268676
0.6917	Remote Similarity	NPC272549
0.6917	Remote Similarity	NPC477549
0.6914	Remote Similarity	NPC469928
0.6914	Remote Similarity	NPC476114
0.6914	Remote Similarity	NPC472027

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 NPC14812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	544
0.2-0.3	693
0.3-0.4	1943
0.4-0.5	2772
0.5-0.6	2297
0.6-0.7	643
0.7-0.8	52
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
0.7336	Intermediate Similarity	NPD7824	Approved
0.7319	Intermediate Similarity	NPD7470	Discontinued
0.7317	Intermediate Similarity	NPD7953	Approved
0.7317	Intermediate Similarity	NPD7952	Approved
0.7317	Intermediate Similarity	NPD7789	Approved
0.7317	Intermediate Similarity	NPD7791	Approved
0.7317	Intermediate Similarity	NPD7951	Approved
0.7317	Intermediate Similarity	NPD7790	Approved
0.7317	Intermediate Similarity	NPD7950	Approved
0.7313	Intermediate Similarity	NPD8459	Approved
0.7313	Intermediate Similarity	NPD8460	Approved
0.7254	Intermediate Similarity	NPD7730	Approved
0.7254	Intermediate Similarity	NPD7731	Approved
0.7253	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8465	Approved
0.7228	Intermediate Similarity	NPD8466	Approved
0.7228	Intermediate Similarity	NPD8467	Approved
0.7224	Intermediate Similarity	NPD7781	Approved
0.7224	Intermediate Similarity	NPD7780	Approved
0.7222	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5003	Discontinued
0.7203	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD8425	Approved
0.7185	Intermediate Similarity	NPD8426	Approved
0.7179	Intermediate Similarity	NPD7001	Phase 3
0.7172	Intermediate Similarity	NPD7271	Approved
0.7164	Intermediate Similarity	NPD8429	Approved
0.7164	Intermediate Similarity	NPD8428	Approved
0.7164	Intermediate Similarity	NPD8427	Approved
0.7155	Intermediate Similarity	NPD7817	Phase 1
0.7137	Intermediate Similarity	NPD8114	Approved
0.7137	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD8115	Approved
0.7106	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD8322	Phase 2
0.7073	Intermediate Similarity	NPD8289	Discontinued
0.7069	Intermediate Similarity	NPD6248	Phase 2
0.7069	Intermediate Similarity	NPD6249	Phase 2
0.7068	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7717	Approved
0.7061	Intermediate Similarity	NPD7716	Approved
0.7059	Intermediate Similarity	NPD7921	Approved
0.7059	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6164	Phase 2
0.7045	Intermediate Similarity	NPD6165	Phase 2
0.7043	Intermediate Similarity	NPD4602	Approved
0.7039	Intermediate Similarity	NPD4600	Approved
0.7039	Intermediate Similarity	NPD4601	Approved
0.7028	Intermediate Similarity	NPD7688	Phase 1
0.7021	Intermediate Similarity	NPD5487	Phase 1
0.7013	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7727	Phase 2
0.7004	Intermediate Similarity	NPD8364	Approved
0.7004	Intermediate Similarity	NPD8363	Approved
0.6996	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6999	Discontinued
0.6992	Remote Similarity	NPD5426	Phase 3
0.6992	Remote Similarity	NPD8098	Approved
0.6992	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7666	Phase 3
0.6975	Remote Similarity	NPD7665	Phase 2
0.6971	Remote Similarity	NPD8094	Discontinued
0.6952	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4897	Phase 2
0.6935	Remote Similarity	NPD7603	Discontinued
0.6932	Remote Similarity	NPD4885	Approved
0.6929	Remote Similarity	NPD8097	Phase 3
0.6929	Remote Similarity	NPD8096	Phase 3
0.6926	Remote Similarity	NPD7878	Phase 2
0.6923	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.692	Remote Similarity	NPD56	Approved
0.692	Remote Similarity	NPD8283	Approved
0.692	Remote Similarity	NPD8282	Approved
0.6913	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6376	Discontinued
0.6897	Remote Similarity	NPD7944	Discontinued
0.6897	Remote Similarity	NPD7619	Phase 3
0.6897	Remote Similarity	NPD7618	Phase 3
0.6883	Remote Similarity	NPD6995	Phase 1
0.686	Remote Similarity	NPD8093	Discontinued
0.6844	Remote Similarity	NPD8489	Phase 1
0.6838	Remote Similarity	NPD6206	Phase 1
0.6833	Remote Similarity	NPD8423	Phase 2
0.6833	Remote Similarity	NPD8399	Phase 1
0.6828	Remote Similarity	NPD5596	Phase 2
0.6826	Remote Similarity	NPD4334	Discontinued
0.6821	Remote Similarity	NPD8349	Phase 1
0.6818	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7946	Pre-registration
0.6809	Remote Similarity	NPD7778	Approved
0.6809	Remote Similarity	NPD7777	Approved
0.6809	Remote Similarity	NPD53	Approved
0.6809	Remote Similarity	NPD6261	Phase 3
0.6807	Remote Similarity	NPD6176	Phase 1
0.68	Remote Similarity	NPD7181	Phase 3
0.6798	Remote Similarity	NPD8119	Discontinued
0.6797	Remote Similarity	NPD2565	Phase 2
0.6797	Remote Similarity	NPD2564	Approved
0.6793	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5901	Discontinued
0.6778	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6596	Phase 2
0.6774	Remote Similarity	NPD5506	Approved
0.6774	Remote Similarity	NPD5507	Approved
0.6767	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6770	Approved
0.6753	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4500	Approved
0.6751	Remote Similarity	NPD4501	Approved
0.674	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7970	Approved
0.6735	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7796	Approved
0.6732	Remote Similarity	NPD7797	Approved
0.6725	Remote Similarity	NPD8421	Discontinued
0.6724	Remote Similarity	NPD4499	Approved
0.6721	Remote Similarity	NPD7573	Discontinued
0.6718	Remote Similarity	NPD4558	Phase 2
0.6707	Remote Similarity	NPD8160	Phase 2
0.6706	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6978	Phase 2
0.6705	Remote Similarity	NPD8016	Phase 3
0.6705	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7956	Approved
0.6704	Remote Similarity	NPD7955	Approved
0.6694	Remote Similarity	NPD2509	Approved
0.6694	Remote Similarity	NPD2510	Approved
0.6693	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8271	Discontinued
0.6679	Remote Similarity	NPD8463	Approved
0.6667	Remote Similarity	NPD6456	Discontinued
0.6667	Remote Similarity	NPD6665	Discontinued
0.6667	Remote Similarity	NPD5444	Phase 1
0.6667	Remote Similarity	NPD4315	Phase 2
0.6667	Remote Similarity	NPD4520	Approved
0.6667	Remote Similarity	NPD7711	Discontinued
0.6667	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5807	Phase 2
0.6641	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8272	Phase 2
0.6638	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7769	Phase 3
0.6627	Remote Similarity	NPD7168	Phase 3
0.6626	Remote Similarity	NPD2916	Discontinued
0.6626	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5913	Phase 3
0.6624	Remote Similarity	NPD8240	Discontinued
0.6617	Remote Similarity	NPD7708	Approved
0.6614	Remote Similarity	NPD8356	Approved
0.6612	Remote Similarity	NPD7568	Phase 1
0.6612	Remote Similarity	NPD7957	Phase 1
0.6612	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7772	Phase 3
0.66	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5835	Phase 3
0.6598	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5834	Phase 3
0.6586	Remote Similarity	NPD5632	Approved
0.6585	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7803	Approved
0.6579	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD8468	Phase 2
0.6577	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7415	Suspended
0.6575	Remote Similarity	NPD8430	Approved
0.6575	Remote Similarity	NPD4086	Phase 1
0.6574	Remote Similarity	NPD7726	Phase 1
0.6573	Remote Similarity	NPD3394	Approved
0.6573	Remote Similarity	NPD3389	Approved
0.6573	Remote Similarity	NPD3393	Approved
0.657	Remote Similarity	NPD8169	Discontinued
0.6566	Remote Similarity	NPD5482	Discontinued
0.6562	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6455	Phase 3
0.6559	Remote Similarity	NPD3243	Approved
0.6556	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD8358	Approved
0.6549	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.654	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2844	Phase 3
0.6531	Remote Similarity	NPD7941	Phase 3

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