NPASS Compound

Structure

CID195192 OpenBabel06191715582D 29 32 0 0 1 0 0 0 0 0999 V2000 1.9657 -2.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3118 -1.1714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 -2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1481 -0.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9394 0.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4891 -2.6151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7820 -1.9080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0351 0.6901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0474 0.5337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 -0.5507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2531 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4891 -0.2009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7351 -1.4080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8718 -3.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3241 -1.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7346 -1.4417 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4891 -2.6151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1962 -0.9080 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1473 -2.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7820 -0.9080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1962 -1.9080 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4891 -0.2009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1473 -0.5990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8910 -0.4540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8632 -3.6695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4563 -3.1681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8904 0.0702 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 6 7 1 0 0 0 0 6 17 2 0 0 0 0 7 21 1 0 0 0 0 8 9 1 0 0 0 0 8 23 1 0 0 0 0 10 15 2 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 26 2 0 0 0 0 16 25 1 6 0 0 0 18 10 1 1 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 1 0 0 0 20 22 1 0 0 0 0 20 27 2 0 0 0 0 21 23 1 6 0 0 0 21 25 1 0 0 0 0 22 17 1 6 0 0 0 23 4 1 6 0 0 0 24 5 1 6 0 0 0 24 28 1 0 0 0 0 25 9 1 6 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.26
Volume:	431.345
LogP:	4.522
LogD:	3.991
LogS:	-5.099
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.545
Synthetic Accessibility Score:	5.654
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.743
MDCK Permeability:	2.0225028492859565e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.333
30% Bioavailability (F30%):	0.295

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	92.45712280273438%
Volume Distribution (VD):	2.212
Pgp-substrate:	4.055172443389893%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.572
CYP2C19-inhibitor:	0.538
CYP2C19-substrate:	0.74
CYP2C9-inhibitor:	0.343
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.478

ADMET: Excretion

Clearance (CL):	5.361
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.415
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.438
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.935
Carcinogencity:	0.251
Eye Corrosion:	0.034
Eye Irritation:	0.111
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC195192

Natural Product ID:	NPC195192
*Common Name:**	6-Epi-Ohpiobolin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MWYYLZRWWNBROW-RXAKKKFQSA-N
Standard InCHI:	InChI=1S/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-/t16-,18-,19-,21+,22-,23+,24+,25-/m0/s1
SMILES:	O=CC1=CC[C@@H]2[C@](C[C@H]3[C@H]1C(=O)C[C@@]3(C)O)(C)CC[C@]12O[C@H](C[C@@H]1C)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252910
PubChem CID:	12303079
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002882] Ophiobolane sesterterpenoids

*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
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395513]
NPO8649	Drechslera gigantea	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16506833]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21902195]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21902195]
NPO13275	Centaurea scabiosa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO2990	Solenostemon scutellarioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8649	Drechslera gigantea	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12794	Hypericum pseudopetiolatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2613	Artemisia ordosica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5756	Amanita abrupta	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16542	Aloe rupestris	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5119.2	Pseudomonas chlororaphis subsp. aureofaciens	Subspecies	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15571	Iphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11651	Parsonsia heterophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16867	Bursera permollis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13275	Centaurea scabiosa	Species	Asteraceae	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	38

Activity Type	# Activity
Organism	38

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3072	Organism	Sonchus oleraceus	Sonchus oleraceus	Activity	>	3.0	mm	PMID[542964]
NPT125	Organism	Chenopodium album	Chenopodium album	Activity	>	3.0	mm	PMID[542964]
NPT3071	Organism	Setaria viridis	Setaria viridis	Activity	>	3.0	mm	PMID[542964]
NPT3073	Organism	Phalaris canariensis	Phalaris canariensis	Activity	>	3.0	mm	PMID[542964]
NPT130	Organism	Digitaria sanguinalis	Digitaria sanguinalis	Activity	>	3.0	mm	PMID[542964]
NPT3070	Organism	Diplotaxis erucoides	Diplotaxis erucoides	Activity	=	2.0	mm	PMID[542964]
NPT131	Organism	Convolvulus arvensis	Convolvulus arvensis	Activity	=	2.0	mm	PMID[542964]
NPT125	Organism	Chenopodium album	Chenopodium album	Activity	=	2.0	mm	PMID[542964]
NPT3073	Organism	Phalaris canariensis	Phalaris canariensis	Activity	=	2.0	mm	PMID[542964]
NPT3074	Organism	Piptatherum miliaceum	Piptatherum miliaceum	Activity	=	2.0	mm	PMID[542964]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Activity	=	2.0	mm	PMID[542964]
NPT130	Organism	Digitaria sanguinalis	Digitaria sanguinalis	Activity	=	2.0	mm	PMID[542964]
NPT3076	Organism	Cynodon dactylon	Cynodon dactylon	Activity	=	2.0	mm	PMID[542964]
NPT3075	Organism	Bromus sterilis	Bromus sterilis	Activity	=	2.0	mm	PMID[542964]
NPT3077	Organism	Avena sterilis subsp. ludoviciana	Avena sterilis subsp. ludoviciana	Activity	=	2.0	mm	PMID[542964]
NPT132	Organism	Amaranthus retroflexus	Amaranthus retroflexus	Activity	=	1.0	mm	PMID[542964]
NPT3073	Organism	Phalaris canariensis	Phalaris canariensis	Activity	=	1.0	mm	PMID[542964]
NPT3074	Organism	Piptatherum miliaceum	Piptatherum miliaceum	Activity	=	1.0	mm	PMID[542964]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Activity	=	1.0	mm	PMID[542964]
NPT3076	Organism	Cynodon dactylon	Cynodon dactylon	Activity	=	1.0	mm	PMID[542964]
NPT3075	Organism	Bromus sterilis	Bromus sterilis	Activity	=	1.0	mm	PMID[542964]

☑ 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 NPC195192 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	244
0.1-0.2	1637
0.2-0.3	6863
0.3-0.4	14500
0.4-0.5	10410
0.5-0.6	6460
0.6-0.7	2370
0.7-0.8	190
0.8-0.85	12
0.85-0.9	9
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304738
0.9082	High Similarity	NPC25639
0.9032	High Similarity	NPC2946
0.8925	High Similarity	NPC41217
0.883	High Similarity	NPC49946
0.883	High Similarity	NPC306168
0.8646	High Similarity	NPC37816
0.8061	Intermediate Similarity	NPC477711
0.8058	Intermediate Similarity	NPC477950
0.8041	Intermediate Similarity	NPC477710
0.7885	Intermediate Similarity	NPC475099
0.7822	Intermediate Similarity	NPC90453
0.78	Intermediate Similarity	NPC290651
0.7767	Intermediate Similarity	NPC477949
0.7767	Intermediate Similarity	NPC170143
0.7767	Intermediate Similarity	NPC213947
0.7767	Intermediate Similarity	NPC108475
0.7714	Intermediate Similarity	NPC171759
0.7706	Intermediate Similarity	NPC474901
0.7706	Intermediate Similarity	NPC475941
0.7692	Intermediate Similarity	NPC471610
0.7692	Intermediate Similarity	NPC109556
0.7664	Intermediate Similarity	NPC294259
0.7624	Intermediate Similarity	NPC261607
0.7624	Intermediate Similarity	NPC300312
0.7624	Intermediate Similarity	NPC221282
0.7624	Intermediate Similarity	NPC111114
0.7615	Intermediate Similarity	NPC177064
0.7604	Intermediate Similarity	NPC20262
0.7604	Intermediate Similarity	NPC256750
0.76	Intermediate Similarity	NPC170775
0.7573	Intermediate Similarity	NPC476487
0.7573	Intermediate Similarity	NPC476488
0.757	Intermediate Similarity	NPC168575
0.7547	Intermediate Similarity	NPC206079
0.7524	Intermediate Similarity	NPC141191
0.75	Intermediate Similarity	NPC126156
0.75	Intermediate Similarity	NPC475970
0.75	Intermediate Similarity	NPC309190
0.75	Intermediate Similarity	NPC185553
0.7477	Intermediate Similarity	NPC179642
0.7477	Intermediate Similarity	NPC118405
0.7476	Intermediate Similarity	NPC469632
0.7476	Intermediate Similarity	NPC298919
0.7476	Intermediate Similarity	NPC167219
0.7474	Intermediate Similarity	NPC301769
0.7453	Intermediate Similarity	NPC280963
0.7451	Intermediate Similarity	NPC284185
0.7449	Intermediate Similarity	NPC475796
0.7431	Intermediate Similarity	NPC60681
0.7429	Intermediate Similarity	NPC169205
0.7426	Intermediate Similarity	NPC232747
0.7426	Intermediate Similarity	NPC123912
0.7419	Intermediate Similarity	NPC251435
0.7404	Intermediate Similarity	NPC90121
0.7404	Intermediate Similarity	NPC474490
0.7404	Intermediate Similarity	NPC67584
0.7404	Intermediate Similarity	NPC48803
0.7404	Intermediate Similarity	NPC193645
0.7404	Intermediate Similarity	NPC275960
0.74	Intermediate Similarity	NPC201658
0.7383	Intermediate Similarity	NPC237190
0.7379	Intermediate Similarity	NPC473273
0.7379	Intermediate Similarity	NPC473234
0.7379	Intermediate Similarity	NPC60386
0.7379	Intermediate Similarity	NPC153590
0.7379	Intermediate Similarity	NPC200237
0.7379	Intermediate Similarity	NPC308656
0.7379	Intermediate Similarity	NPC473263
0.7379	Intermediate Similarity	NPC125180
0.7374	Intermediate Similarity	NPC125290
0.7368	Intermediate Similarity	NPC238667
0.7364	Intermediate Similarity	NPC220974
0.7358	Intermediate Similarity	NPC477355
0.7358	Intermediate Similarity	NPC222011
0.7353	Intermediate Similarity	NPC253144
0.7353	Intermediate Similarity	NPC301969
0.7353	Intermediate Similarity	NPC37607
0.7333	Intermediate Similarity	NPC142529
0.7333	Intermediate Similarity	NPC213078
0.7333	Intermediate Similarity	NPC9812
0.7333	Intermediate Similarity	NPC91771
0.7327	Intermediate Similarity	NPC475906
0.7327	Intermediate Similarity	NPC469631
0.7327	Intermediate Similarity	NPC471047
0.7327	Intermediate Similarity	NPC469653
0.7327	Intermediate Similarity	NPC469628
0.7321	Intermediate Similarity	NPC470496
0.7308	Intermediate Similarity	NPC477241
0.7304	Intermediate Similarity	NPC469794
0.7304	Intermediate Similarity	NPC72772
0.7297	Intermediate Similarity	NPC10150
0.7292	Intermediate Similarity	NPC32758
0.7292	Intermediate Similarity	NPC469690
0.7292	Intermediate Similarity	NPC261125
0.7292	Intermediate Similarity	NPC181195
0.7292	Intermediate Similarity	NPC469620
0.7282	Intermediate Similarity	NPC70595
0.7282	Intermediate Similarity	NPC150978
0.7282	Intermediate Similarity	NPC74103
0.7282	Intermediate Similarity	NPC472705
0.7282	Intermediate Similarity	NPC123177
0.7281	Intermediate Similarity	NPC9848
0.7281	Intermediate Similarity	NPC312017
0.7273	Intermediate Similarity	NPC253223
0.7273	Intermediate Similarity	NPC238197
0.7264	Intermediate Similarity	NPC87090
0.7264	Intermediate Similarity	NPC69385
0.7264	Intermediate Similarity	NPC239895
0.7264	Intermediate Similarity	NPC161493
0.7263	Intermediate Similarity	NPC276769
0.7257	Intermediate Similarity	NPC474750
0.7255	Intermediate Similarity	NPC12872
0.7255	Intermediate Similarity	NPC168679
0.7255	Intermediate Similarity	NPC477215
0.7255	Intermediate Similarity	NPC476388
0.725	Intermediate Similarity	NPC144625
0.7248	Intermediate Similarity	NPC470839
0.7248	Intermediate Similarity	NPC176883
0.7248	Intermediate Similarity	NPC110989
0.7248	Intermediate Similarity	NPC474775
0.7241	Intermediate Similarity	NPC474518
0.7241	Intermediate Similarity	NPC475305
0.7241	Intermediate Similarity	NPC239273
0.7241	Intermediate Similarity	NPC36754
0.7238	Intermediate Similarity	NPC52044
0.7238	Intermediate Similarity	NPC472469
0.7232	Intermediate Similarity	NPC187876
0.7228	Intermediate Similarity	NPC471657
0.7228	Intermediate Similarity	NPC45957
0.7222	Intermediate Similarity	NPC185141
0.7222	Intermediate Similarity	NPC110443
0.7222	Intermediate Similarity	NPC46998
0.7222	Intermediate Similarity	NPC133907
0.7222	Intermediate Similarity	NPC128733
0.7222	Intermediate Similarity	NPC477356
0.7222	Intermediate Similarity	NPC116139
0.7216	Intermediate Similarity	NPC164218
0.7212	Intermediate Similarity	NPC135776
0.7212	Intermediate Similarity	NPC229976
0.7196	Intermediate Similarity	NPC470188
0.7196	Intermediate Similarity	NPC64742
0.7196	Intermediate Similarity	NPC244411
0.7193	Intermediate Similarity	NPC100267
0.7193	Intermediate Similarity	NPC475524
0.7193	Intermediate Similarity	NPC285956
0.7193	Intermediate Similarity	NPC221144
0.7193	Intermediate Similarity	NPC69291
0.7184	Intermediate Similarity	NPC77337
0.7184	Intermediate Similarity	NPC145666
0.7184	Intermediate Similarity	NPC71533
0.7184	Intermediate Similarity	NPC106510
0.7182	Intermediate Similarity	NPC100487
0.7182	Intermediate Similarity	NPC203659
0.7182	Intermediate Similarity	NPC13385
0.7179	Intermediate Similarity	NPC161060
0.7179	Intermediate Similarity	NPC475372
0.7179	Intermediate Similarity	NPC475401
0.7172	Intermediate Similarity	NPC62214
0.7172	Intermediate Similarity	NPC474748
0.717	Intermediate Similarity	NPC472674
0.717	Intermediate Similarity	NPC18019
0.717	Intermediate Similarity	NPC93271
0.717	Intermediate Similarity	NPC135576
0.717	Intermediate Similarity	NPC121036
0.717	Intermediate Similarity	NPC24956
0.7168	Intermediate Similarity	NPC477103
0.7168	Intermediate Similarity	NPC99760
0.7158	Intermediate Similarity	NPC226242
0.7158	Intermediate Similarity	NPC469646
0.7158	Intermediate Similarity	NPC215481
0.7157	Intermediate Similarity	NPC58532
0.7157	Intermediate Similarity	NPC476708
0.7157	Intermediate Similarity	NPC472677
0.7156	Intermediate Similarity	NPC70369
0.7156	Intermediate Similarity	NPC87351
0.7156	Intermediate Similarity	NPC66110
0.7156	Intermediate Similarity	NPC185530
0.7156	Intermediate Similarity	NPC225353
0.7155	Intermediate Similarity	NPC196931
0.7143	Intermediate Similarity	NPC289004
0.7143	Intermediate Similarity	NPC476415
0.7143	Intermediate Similarity	NPC477131
0.7143	Intermediate Similarity	NPC65829
0.7143	Intermediate Similarity	NPC127019
0.7143	Intermediate Similarity	NPC53685
0.713	Intermediate Similarity	NPC209058
0.713	Intermediate Similarity	NPC174314
0.713	Intermediate Similarity	NPC476274
0.7129	Intermediate Similarity	NPC279859
0.7129	Intermediate Similarity	NPC238593
0.7129	Intermediate Similarity	NPC38576
0.7129	Intermediate Similarity	NPC469676
0.7129	Intermediate Similarity	NPC261253
0.7129	Intermediate Similarity	NPC474045
0.7129	Intermediate Similarity	NPC261721
0.7119	Intermediate Similarity	NPC477092
0.7119	Intermediate Similarity	NPC312536
0.7117	Intermediate Similarity	NPC1679
0.7115	Intermediate Similarity	NPC190442

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 NPC195192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	2332
0.2-0.3	4147
0.3-0.4	1770
0.4-0.5	357
0.5-0.6	209
0.6-0.7	106
0.7-0.8	2
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
0.77	Intermediate Similarity	NPD5785	Approved
0.7404	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5786	Approved
0.72	Intermediate Similarity	NPD5363	Approved
0.7054	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6371	Approved
0.697	Remote Similarity	NPD5369	Approved
0.69	Remote Similarity	NPD4269	Approved
0.69	Remote Similarity	NPD4270	Approved
0.6852	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD7320	Approved
0.6832	Remote Similarity	NPD5362	Discontinued
0.6822	Remote Similarity	NPD5282	Discontinued
0.681	Remote Similarity	NPD6650	Approved
0.681	Remote Similarity	NPD6649	Approved
0.6783	Remote Similarity	NPD6373	Approved
0.6783	Remote Similarity	NPD6372	Approved
0.6752	Remote Similarity	NPD6053	Discontinued
0.6733	Remote Similarity	NPD6435	Approved
0.6733	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4252	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD6079	Approved
0.6636	Remote Similarity	NPD4755	Approved
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6635	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4790	Discontinued
0.6614	Remote Similarity	NPD7319	Approved
0.6609	Remote Similarity	NPD5697	Approved
0.6607	Remote Similarity	NPD5223	Approved
0.6606	Remote Similarity	NPD4629	Approved
0.6606	Remote Similarity	NPD5695	Phase 3
0.6606	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5210	Approved
0.6604	Remote Similarity	NPD4753	Phase 2
0.6604	Remote Similarity	NPD5328	Approved
0.6602	Remote Similarity	NPD3666	Approved
0.6602	Remote Similarity	NPD3665	Phase 1
0.6602	Remote Similarity	NPD3133	Approved
0.6587	Remote Similarity	NPD7078	Approved
0.6581	Remote Similarity	NPD7290	Approved
0.6581	Remote Similarity	NPD6883	Approved
0.6581	Remote Similarity	NPD7102	Approved
0.6579	Remote Similarity	NPD5141	Approved
0.6577	Remote Similarity	NPD5696	Approved
0.6574	Remote Similarity	NPD6399	Phase 3
0.6569	Remote Similarity	NPD4221	Approved
0.6569	Remote Similarity	NPD4223	Phase 3
0.6569	Remote Similarity	NPD5209	Approved
0.6552	Remote Similarity	NPD6011	Approved
0.6549	Remote Similarity	NPD4633	Approved
0.6549	Remote Similarity	NPD5226	Approved
0.6549	Remote Similarity	NPD5224	Approved
0.6549	Remote Similarity	NPD5225	Approved
0.6538	Remote Similarity	NPD5329	Approved
0.6538	Remote Similarity	NPD1694	Approved
0.6535	Remote Similarity	NPD5368	Approved
0.6532	Remote Similarity	NPD6370	Approved
0.6525	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD6617	Approved
0.6525	Remote Similarity	NPD8130	Phase 1
0.6525	Remote Similarity	NPD6847	Approved
0.6522	Remote Similarity	NPD6008	Approved
0.6518	Remote Similarity	NPD4700	Approved
0.6508	Remote Similarity	NPD7507	Approved
0.6505	Remote Similarity	NPD5331	Approved
0.6505	Remote Similarity	NPD5332	Approved
0.6504	Remote Similarity	NPD6059	Approved
0.6496	Remote Similarity	NPD6012	Approved
0.6496	Remote Similarity	NPD6013	Approved
0.6496	Remote Similarity	NPD6014	Approved
0.6491	Remote Similarity	NPD5174	Approved
0.6491	Remote Similarity	NPD5175	Approved
0.6481	Remote Similarity	NPD5693	Phase 1
0.6476	Remote Similarity	NPD7146	Approved
0.6476	Remote Similarity	NPD5330	Approved
0.6476	Remote Similarity	NPD6684	Approved
0.6476	Remote Similarity	NPD5690	Phase 2
0.6476	Remote Similarity	NPD7521	Approved
0.6476	Remote Similarity	NPD7334	Approved
0.6476	Remote Similarity	NPD6409	Approved
0.6471	Remote Similarity	NPD6882	Approved
0.6471	Remote Similarity	NPD8297	Approved
0.6466	Remote Similarity	NPD5701	Approved
0.6452	Remote Similarity	NPD6015	Approved
0.6452	Remote Similarity	NPD6016	Approved
0.6449	Remote Similarity	NPD1695	Approved
0.6442	Remote Similarity	NPD4197	Approved
0.6441	Remote Similarity	NPD4634	Approved
0.6429	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD7492	Approved
0.6429	Remote Similarity	NPD7638	Approved
0.6422	Remote Similarity	NPD4202	Approved
0.6408	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5988	Approved
0.6396	Remote Similarity	NPD5222	Approved
0.6396	Remote Similarity	NPD5221	Approved
0.6396	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5207	Approved
0.6387	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6616	Approved
0.6372	Remote Similarity	NPD7639	Approved
0.6372	Remote Similarity	NPD7640	Approved
0.6355	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4754	Approved
0.6346	Remote Similarity	NPD4788	Approved
0.6339	Remote Similarity	NPD5173	Approved
0.633	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD5284	Approved
0.6321	Remote Similarity	NPD5280	Approved
0.6321	Remote Similarity	NPD4689	Approved
0.6321	Remote Similarity	NPD4694	Approved
0.6321	Remote Similarity	NPD5205	Approved
0.6321	Remote Similarity	NPD4688	Approved
0.6321	Remote Similarity	NPD3618	Phase 1
0.6321	Remote Similarity	NPD4690	Approved
0.6321	Remote Similarity	NPD5279	Phase 3
0.6321	Remote Similarity	NPD4693	Phase 3
0.6321	Remote Similarity	NPD4138	Approved
0.632	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6673	Approved
0.6296	Remote Similarity	NPD6080	Approved
0.6296	Remote Similarity	NPD6904	Approved
0.6286	Remote Similarity	NPD4786	Approved
0.6279	Remote Similarity	NPD7736	Approved
0.6271	Remote Similarity	NPD5128	Approved
0.6271	Remote Similarity	NPD4729	Approved
0.6271	Remote Similarity	NPD4730	Approved
0.624	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD4767	Approved
0.6216	Remote Similarity	NPD6001	Approved
0.6214	Remote Similarity	NPD4819	Approved
0.6214	Remote Similarity	NPD4821	Approved
0.6214	Remote Similarity	NPD4822	Approved
0.6214	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4820	Approved
0.6211	Remote Similarity	NPD7331	Phase 2
0.621	Remote Similarity	NPD6335	Approved
0.6204	Remote Similarity	NPD6672	Approved
0.6204	Remote Similarity	NPD5737	Approved
0.6204	Remote Similarity	NPD4518	Approved
0.6202	Remote Similarity	NPD8293	Discontinued
0.619	Remote Similarity	NPD7154	Phase 3
0.6182	Remote Similarity	NPD6050	Approved
0.6182	Remote Similarity	NPD6411	Approved
0.6179	Remote Similarity	NPD6274	Approved
0.6167	Remote Similarity	NPD5250	Approved
0.6167	Remote Similarity	NPD5249	Phase 3
0.6167	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD5248	Approved
0.6167	Remote Similarity	NPD5169	Approved
0.6167	Remote Similarity	NPD5135	Approved
0.6167	Remote Similarity	NPD5247	Approved
0.6167	Remote Similarity	NPD5251	Approved
0.616	Remote Similarity	NPD7100	Approved
0.616	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD6033	Approved
0.6148	Remote Similarity	NPD4632	Approved
0.6147	Remote Similarity	NPD6051	Approved
0.6129	Remote Similarity	NPD6317	Approved
0.6126	Remote Similarity	NPD5778	Approved
0.6126	Remote Similarity	NPD5779	Approved
0.6117	Remote Similarity	NPD4195	Approved
0.6116	Remote Similarity	NPD5216	Approved
0.6116	Remote Similarity	NPD5217	Approved
0.6116	Remote Similarity	NPD5127	Approved
0.6116	Remote Similarity	NPD5215	Approved
0.6111	Remote Similarity	NPD4251	Approved
0.6111	Remote Similarity	NPD4250	Approved
0.6105	Remote Similarity	NPD7341	Phase 2
0.6095	Remote Similarity	NPD3667	Approved
0.6091	Remote Similarity	NPD5692	Phase 3
0.6091	Remote Similarity	NPD4096	Approved
0.608	Remote Similarity	NPD6313	Approved
0.608	Remote Similarity	NPD6314	Approved
0.6075	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6052	Approved
0.6055	Remote Similarity	NPD5208	Approved
0.6053	Remote Similarity	NPD7902	Approved
0.605	Remote Similarity	NPD6412	Phase 2
0.6036	Remote Similarity	NPD5694	Approved
0.6036	Remote Similarity	NPD7637	Suspended
0.6019	Remote Similarity	NPD4271	Approved
0.6019	Remote Similarity	NPD6098	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