NPASS Compound

Structure

NPC239763 OpenBabel07101719132D 56 63 0 0 0 0 0 0 0 0999 V2000 -1.2435 -3.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5306 -4.7076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7191 -4.4098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5744 -4.2918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8615 -5.4507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3124 -5.3233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8908 -3.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8689 -3.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3014 -5.1143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3406 -0.6511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5161 -2.2691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2216 -3.7565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7136 -4.3052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8834 -5.2428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9338 -1.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5216 -2.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9001 -6.1323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8947 -6.0278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3351 -0.5465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9229 -1.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1203 -3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1149 -3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2142 -5.9860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4934 -7.0459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4824 -6.8368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7418 0.3670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9174 -1.2510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7027 -4.0962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 17 2 0 0 0 0 2 6 2 0 0 0 0 2 17 1 0 0 0 0 3 7 2 0 0 0 0 3 18 1 0 0 0 0 4 8 2 0 0 0 0 4 19 1 0 0 0 0 5 20 2 0 0 0 0 6 20 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 41 1 0 0 0 0 11 18 2 0 0 0 0 11 27 1 0 0 0 0 12 19 2 0 0 0 0 12 32 1 0 0 0 0 13 21 2 0 0 0 0 13 28 1 0 0 0 0 14 22 2 0 0 0 0 14 29 1 0 0 0 0 15 23 2 0 0 0 0 15 30 1 0 0 0 0 16 24 2 0 0 0 0 16 31 1 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 20 42 1 0 0 0 0 21 23 1 0 0 0 0 21 35 1 0 0 0 0 22 24 1 0 0 0 0 22 36 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 0 0 0 0 25 27 2 0 0 0 0 25 43 1 0 0 0 0 26 32 2 0 0 0 0 26 44 1 0 0 0 0 27 45 1 0 0 0 0 28 30 2 0 0 0 0 28 46 1 0 0 0 0 29 31 2 0 0 0 0 29 47 1 0 0 0 0 30 48 1 0 0 0 0 31 49 1 0 0 0 0 32 55 1 0 0 0 0 33 37 2 0 0 0 0 33 39 1 0 0 0 0 34 38 2 0 0 0 0 34 40 1 0 0 0 0 35 36 2 0 0 0 0 35 37 1 0 0 0 0 36 38 1 0 0 0 0 37 41 1 0 0 0 0 38 41 1 0 0 0 0 39 50 2 0 0 0 0 40 51 2 0 0 0 0 52 56 1 0 0 0 0 53 56 2 0 0 0 0 54 56 2 0 0 0 0 55 56 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	777.12
Volume:	731.784
LogP:	5.475
LogD:	2.192
LogS:	-4.367
# Rotatable Bonds:	7
TPSA:	264.51
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	8
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.039
Synthetic Accessibility Score:	3.88
Fsp3:	0.05
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	3

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.521
MDCK Permeability:	6.453458354371833e-06
Pgp-inhibitor:	0.067
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.99
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	100.19869232177734%
Volume Distribution (VD):	-0.259
Pgp-substrate:	3.4513604640960693%

ADMET: Metabolism

CYP1A2-inhibitor:	0.912
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.308
CYP2C19-substrate:	0.031
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.578
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.026

ADMET: Excretion

Clearance (CL):	5.196
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.441
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.966
Carcinogencity:	0.864
Eye Corrosion:	0.003
Eye Irritation:	0.932
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC239763

Natural Product ID:	NPC239763
*Common Name:**	Baculiferin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RSCDHCTUBRPIPB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C40H27NO14S/c42-20-5-1-17(2-6-20)9-10-41-37-33(18-3-7-25(43)27(45)11-18)39(50)23-15-30(48)28(46)13-21(23)35(37)36-22-14-29(47)31(49)16-24(22)40(51)34(38(36)41)19-4-8-26(44)32(12-19)55-56(52,53)54/h1-8,11-16,42-49H,9-10H2,(H,52,53,54)
SMILES:	Oc1ccc(cc1)CCn1c2=C(c3ccc(c(c3)O)O)C(=O)c3c(c2c2c1=C(c1ccc(c(c1)OS(=O)(=O)O)O)C(=O)c1c2cc(c(c1)O)O)cc(c(c3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1214279
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	Chinese	n.a.	n.a.	PMID[20624681]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	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
MIC	2
Others	3

Activity Type	# Activity
Individual Protein	1
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	RU	=	89.7	pg/mm2	PMID[469794]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	12.5	ug.mL-1	PMID[469794]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[469794]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	2.2	ug.mL-1	PMID[469794]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	1.3	ug.mL-1	PMID[469794]
NPT2	Others	Unspecified		RU	=	152.4	pg/mm2	PMID[469794]
NPT2	Others	Unspecified		RU	=	12.9	pg/mm2	PMID[469794]

☑ 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 NPC239763 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	427
0.1-0.2	2261
0.2-0.3	10448
0.3-0.4	6597
0.4-0.5	12449
0.5-0.6	9231
0.6-0.7	1203
0.7-0.8	69
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC190401
0.9896	High Similarity	NPC298840
0.9896	High Similarity	NPC303384
0.9896	High Similarity	NPC268393
0.9896	High Similarity	NPC13599
0.9896	High Similarity	NPC191088
0.9896	High Similarity	NPC3214
0.9789	High Similarity	NPC124086
0.9594	High Similarity	NPC121069
0.9391	High Similarity	NPC246658
0.7755	Intermediate Similarity	NPC256935
0.75	Intermediate Similarity	NPC271792
0.7291	Intermediate Similarity	NPC73555
0.7273	Intermediate Similarity	NPC146976
0.7265	Intermediate Similarity	NPC15406
0.7261	Intermediate Similarity	NPC129897
0.7253	Intermediate Similarity	NPC210296
0.7238	Intermediate Similarity	NPC146724
0.7227	Intermediate Similarity	NPC236668
0.7217	Intermediate Similarity	NPC472284
0.7178	Intermediate Similarity	NPC318068
0.7162	Intermediate Similarity	NPC24019
0.7155	Intermediate Similarity	NPC302807
0.7155	Intermediate Similarity	NPC77878
0.7143	Intermediate Similarity	NPC471448
0.7143	Intermediate Similarity	NPC22481
0.7124	Intermediate Similarity	NPC210434
0.7123	Intermediate Similarity	NPC61038
0.7111	Intermediate Similarity	NPC276657
0.7091	Intermediate Similarity	NPC470020
0.7089	Intermediate Similarity	NPC473814
0.7089	Intermediate Similarity	NPC78767
0.7087	Intermediate Similarity	NPC278525
0.7083	Intermediate Similarity	NPC183537
0.7075	Intermediate Similarity	NPC93390
0.7064	Intermediate Similarity	NPC175602
0.7062	Intermediate Similarity	NPC56170
0.7051	Intermediate Similarity	NPC182907
0.7051	Intermediate Similarity	NPC189903
0.7043	Intermediate Similarity	NPC246381
0.7039	Intermediate Similarity	NPC253675
0.7033	Intermediate Similarity	NPC206186
0.7019	Intermediate Similarity	NPC241025
0.7017	Intermediate Similarity	NPC208522
0.7012	Intermediate Similarity	NPC181081
0.7009	Intermediate Similarity	NPC108342
0.7004	Intermediate Similarity	NPC132385
0.6996	Remote Similarity	NPC207866
0.6996	Remote Similarity	NPC329631
0.6986	Remote Similarity	NPC472287
0.6986	Remote Similarity	NPC472286
0.6966	Remote Similarity	NPC90875
0.6966	Remote Similarity	NPC208898
0.6962	Remote Similarity	NPC49672
0.696	Remote Similarity	NPC14686
0.6955	Remote Similarity	NPC53344
0.6951	Remote Similarity	NPC110182
0.6946	Remote Similarity	NPC160898
0.6943	Remote Similarity	NPC94842
0.693	Remote Similarity	NPC74153
0.692	Remote Similarity	NPC232225
0.6916	Remote Similarity	NPC269270
0.6906	Remote Similarity	NPC9894
0.6906	Remote Similarity	NPC220337
0.6903	Remote Similarity	NPC27041
0.6903	Remote Similarity	NPC293151
0.688	Remote Similarity	NPC233334
0.6878	Remote Similarity	NPC166722
0.6875	Remote Similarity	NPC124313
0.6872	Remote Similarity	NPC204446
0.6869	Remote Similarity	NPC473821
0.6867	Remote Similarity	NPC476996
0.6867	Remote Similarity	NPC476998
0.6862	Remote Similarity	NPC84164
0.6862	Remote Similarity	NPC207283
0.686	Remote Similarity	NPC164340
0.6857	Remote Similarity	NPC295158
0.6856	Remote Similarity	NPC253314
0.6847	Remote Similarity	NPC100573
0.6847	Remote Similarity	NPC207873
0.6838	Remote Similarity	NPC289905
0.6838	Remote Similarity	NPC316065
0.6835	Remote Similarity	NPC476995
0.6831	Remote Similarity	NPC51854
0.6824	Remote Similarity	NPC476994
0.6824	Remote Similarity	NPC476997
0.6816	Remote Similarity	NPC472588
0.6814	Remote Similarity	NPC237740
0.6812	Remote Similarity	NPC469439
0.681	Remote Similarity	NPC214980
0.68	Remote Similarity	NPC219087
0.68	Remote Similarity	NPC202605
0.68	Remote Similarity	NPC112206
0.6797	Remote Similarity	NPC51388
0.679	Remote Similarity	NPC270515
0.679	Remote Similarity	NPC9729
0.6784	Remote Similarity	NPC322064
0.6778	Remote Similarity	NPC41501
0.6771	Remote Similarity	NPC171787
0.677	Remote Similarity	NPC279589
0.6766	Remote Similarity	NPC474701
0.6766	Remote Similarity	NPC475596
0.6766	Remote Similarity	NPC316841
0.6766	Remote Similarity	NPC475303
0.6763	Remote Similarity	NPC475648
0.6761	Remote Similarity	NPC472589
0.6761	Remote Similarity	NPC183805
0.6756	Remote Similarity	NPC23294
0.6753	Remote Similarity	NPC16352
0.6753	Remote Similarity	NPC118121
0.6753	Remote Similarity	NPC127720
0.6753	Remote Similarity	NPC220851
0.6753	Remote Similarity	NPC127026
0.6747	Remote Similarity	NPC191489
0.6747	Remote Similarity	NPC89549
0.6744	Remote Similarity	NPC45048
0.6743	Remote Similarity	NPC17677
0.6743	Remote Similarity	NPC102008
0.6741	Remote Similarity	NPC325297
0.6739	Remote Similarity	NPC54066
0.6738	Remote Similarity	NPC470018
0.6737	Remote Similarity	NPC207686
0.6737	Remote Similarity	NPC30456
0.6726	Remote Similarity	NPC283117
0.6724	Remote Similarity	NPC471980
0.6721	Remote Similarity	NPC478045
0.6715	Remote Similarity	NPC139763
0.6711	Remote Similarity	NPC303951
0.6711	Remote Similarity	NPC290689
0.6709	Remote Similarity	NPC124029
0.6709	Remote Similarity	NPC211920
0.6709	Remote Similarity	NPC74575
0.6708	Remote Similarity	NPC107123
0.6697	Remote Similarity	NPC90229
0.6696	Remote Similarity	NPC210828
0.6696	Remote Similarity	NPC149471
0.6696	Remote Similarity	NPC90185
0.6696	Remote Similarity	NPC48317
0.6696	Remote Similarity	NPC39679
0.6696	Remote Similarity	NPC271215
0.6696	Remote Similarity	NPC86834
0.6694	Remote Similarity	NPC134637
0.6682	Remote Similarity	NPC44354
0.6681	Remote Similarity	NPC294375
0.6681	Remote Similarity	NPC39370
0.6681	Remote Similarity	NPC475406
0.668	Remote Similarity	NPC475844
0.6667	Remote Similarity	NPC132329
0.6667	Remote Similarity	NPC280964
0.6667	Remote Similarity	NPC49547
0.6667	Remote Similarity	NPC114335
0.6667	Remote Similarity	NPC141915
0.6667	Remote Similarity	NPC473506
0.6653	Remote Similarity	NPC326363
0.6653	Remote Similarity	NPC38959
0.6653	Remote Similarity	NPC327904
0.6653	Remote Similarity	NPC477549
0.6652	Remote Similarity	NPC471489
0.6652	Remote Similarity	NPC270918
0.6652	Remote Similarity	NPC155792
0.664	Remote Similarity	NPC100734
0.664	Remote Similarity	NPC88923
0.664	Remote Similarity	NPC315634
0.6639	Remote Similarity	NPC255800
0.6639	Remote Similarity	NPC253482
0.6639	Remote Similarity	NPC172222
0.6639	Remote Similarity	NPC96584
0.6638	Remote Similarity	NPC476110
0.6638	Remote Similarity	NPC475631
0.6638	Remote Similarity	NPC228377
0.6638	Remote Similarity	NPC328186
0.6638	Remote Similarity	NPC475600
0.6638	Remote Similarity	NPC122968
0.6638	Remote Similarity	NPC477787
0.6638	Remote Similarity	NPC87152
0.6636	Remote Similarity	NPC5374
0.6636	Remote Similarity	NPC280714
0.6624	Remote Similarity	NPC328154
0.6624	Remote Similarity	NPC201508
0.6624	Remote Similarity	NPC150698
0.6624	Remote Similarity	NPC473449
0.6624	Remote Similarity	NPC477902
0.6624	Remote Similarity	NPC96801
0.6623	Remote Similarity	NPC84815
0.6623	Remote Similarity	NPC301368
0.6623	Remote Similarity	NPC216428
0.6611	Remote Similarity	NPC327769
0.661	Remote Similarity	NPC471977
0.661	Remote Similarity	NPC470486
0.661	Remote Similarity	NPC475644
0.661	Remote Similarity	NPC471190
0.661	Remote Similarity	NPC274640
0.6609	Remote Similarity	NPC122463
0.6599	Remote Similarity	NPC473188
0.6597	Remote Similarity	NPC473186
0.6594	Remote Similarity	NPC118228
0.6592	Remote Similarity	NPC134848
0.659	Remote Similarity	NPC133140
0.659	Remote Similarity	NPC195268
0.659	Remote Similarity	NPC99666

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 NPC239763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	671
0.2-0.3	811
0.3-0.4	1357
0.4-0.5	3233
0.5-0.6	2446
0.6-0.7	370
0.7-0.8	4
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
0.7294	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7395	Discontinued
0.7033	Intermediate Similarity	NPD4948	Discontinued
0.7013	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD8091	Phase 3
0.7	Intermediate Similarity	NPD6376	Discontinued
0.7	Intermediate Similarity	NPD4845	Discontinued
0.6996	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5866	Approved
0.6938	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7994	Phase 2
0.6851	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD2916	Discontinued
0.6838	Remote Similarity	NPD6962	Phase 2
0.6824	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1483	Discontinued
0.6792	Remote Similarity	NPD6716	Phase 1
0.6762	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7417	Discontinued
0.6747	Remote Similarity	NPD7708	Approved
0.6743	Remote Similarity	NPD7778	Approved
0.6743	Remote Similarity	NPD53	Approved
0.6743	Remote Similarity	NPD7777	Approved
0.6733	Remote Similarity	NPD6456	Discontinued
0.6725	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD8016	Phase 3
0.6697	Remote Similarity	NPD7948	Phase 1
0.6683	Remote Similarity	NPD2781	Approved
0.6667	Remote Similarity	NPD3746	Discontinued
0.6652	Remote Similarity	NPD7222	Phase 2
0.664	Remote Similarity	NPD7803	Approved
0.6639	Remote Similarity	NPD4373	Phase 2
0.6638	Remote Similarity	NPD8149	Discontinued
0.6638	Remote Similarity	NPD3259	Approved
0.6637	Remote Similarity	NPD6987	Phase 1
0.6623	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6975	Discontinued
0.6606	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7180	Phase 3
0.6594	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.659	Remote Similarity	NPD3923	Approved
0.659	Remote Similarity	NPD3922	Approved
0.659	Remote Similarity	NPD3921	Approved
0.659	Remote Similarity	NPD3924	Approved
0.6585	Remote Similarity	NPD2782	Approved
0.6585	Remote Similarity	NPD2780	Approved
0.658	Remote Similarity	NPD7878	Phase 2
0.6578	Remote Similarity	NPD5429	Discontinued
0.6578	Remote Similarity	NPD7453	Approved
0.6578	Remote Similarity	NPD7452	Approved
0.6562	Remote Similarity	NPD5901	Discontinued
0.6556	Remote Similarity	NPD5805	Approved
0.6552	Remote Similarity	NPD3258	Approved
0.6546	Remote Similarity	NPD8463	Approved
0.654	Remote Similarity	NPD3920	Phase 2
0.6532	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.653	Remote Similarity	NPD4418	Discontinued
0.6524	Remote Similarity	NPD6242	Discontinued
0.6522	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6517	Phase 3
0.6515	Remote Similarity	NPD7853	Phase 2
0.6514	Remote Similarity	NPD5968	Phase 3
0.6513	Remote Similarity	NPD4952	Phase 3
0.6511	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1643	Phase 3
0.6504	Remote Similarity	NPD5488	Discontinued
0.6498	Remote Similarity	NPD6836	Approved
0.6498	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5914	Approved
0.6486	Remote Similarity	NPD8395	Approved
0.6486	Remote Similarity	NPD5608	Approved
0.6486	Remote Similarity	NPD8396	Approved
0.6486	Remote Similarity	NPD5609	Approved
0.6485	Remote Similarity	NPD8238	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3763	Approved
0.6481	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7654	Discontinued
0.6468	Remote Similarity	NPD6995	Phase 1
0.6466	Remote Similarity	NPD4989	Phase 2
0.6463	Remote Similarity	NPD7921	Approved
0.6462	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7924	Phase 2
0.6459	Remote Similarity	NPD7925	Phase 2
0.6457	Remote Similarity	NPD484	Approved
0.6456	Remote Similarity	NPD1631	Approved
0.6452	Remote Similarity	NPD8102	Discontinued
0.6452	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7956	Approved
0.6443	Remote Similarity	NPD7955	Approved
0.6438	Remote Similarity	NPD3354	Phase 2
0.6435	Remote Similarity	NPD7069	Discontinued
0.6435	Remote Similarity	NPD3815	Phase 1
0.6435	Remote Similarity	NPD8093	Discontinued
0.6435	Remote Similarity	NPD3816	Phase 1
0.6434	Remote Similarity	NPD4561	Discontinued
0.6432	Remote Similarity	NPD5445	Approved
0.6429	Remote Similarity	NPD4328	Approved
0.6429	Remote Similarity	NPD4511	Phase 1
0.6422	Remote Similarity	NPD6733	Discontinued
0.6419	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6790	Phase 1
0.6407	Remote Similarity	NPD8094	Discontinued
0.6398	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD3263	Phase 3
0.6383	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD3257	Approved
0.6379	Remote Similarity	NPD4897	Phase 2
0.6368	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD7885	Phase 2
0.6367	Remote Similarity	NPD7886	Phase 2
0.6364	Remote Similarity	NPD7922	Phase 1
0.6364	Remote Similarity	NPD7181	Phase 3
0.636	Remote Similarity	NPD7588	Discontinued
0.636	Remote Similarity	NPD3809	Discontinued
0.6356	Remote Similarity	NPD5507	Approved
0.6356	Remote Similarity	NPD5506	Approved
0.6355	Remote Similarity	NPD6452	Discontinued
0.6355	Remote Similarity	NPD3229	Phase 2
0.6347	Remote Similarity	NPD5928	Phase 1
0.6345	Remote Similarity	NPD7719	Discontinued
0.6345	Remote Similarity	NPD3925	Approved
0.6343	Remote Similarity	NPD7546	Discontinued
0.634	Remote Similarity	NPD6974	Phase 3
0.6339	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6999	Discontinued
0.6339	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5050	Approved
0.6338	Remote Similarity	NPD6159	Phase 2
0.6336	Remote Similarity	NPD3243	Approved
0.6333	Remote Similarity	NPD1575	Approved
0.6333	Remote Similarity	NPD7767	Approved
0.6333	Remote Similarity	NPD1573	Approved
0.6332	Remote Similarity	NPD7300	Phase 3
0.6332	Remote Similarity	NPD4859	Phase 1
0.6332	Remote Similarity	NPD7302	Phase 3
0.6329	Remote Similarity	NPD8356	Approved
0.6326	Remote Similarity	NPD5027	Approved
0.6326	Remote Similarity	NPD5031	Approved
0.6326	Remote Similarity	NPD5029	Approved
0.6325	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4885	Approved
0.632	Remote Similarity	NPD7658	Phase 2
0.632	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD7603	Discontinued
0.6316	Remote Similarity	NPD6807	Phase 3
0.6311	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1630	Approved
0.6309	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7301	Phase 3
0.629	Remote Similarity	NPD5937	Approved
0.629	Remote Similarity	NPD4941	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD5809	Phase 3
0.6282	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD5512	Phase 3
0.6277	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4312	Approved
0.627	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD2421	Approved
0.6269	Remote Similarity	NPD2420	Approved
0.6265	Remote Similarity	NPD3959	Phase 2
0.6265	Remote Similarity	NPD3962	Phase 2
0.6261	Remote Similarity	NPD7665	Phase 2
0.6261	Remote Similarity	NPD7666	Phase 3
0.6261	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7187	Phase 2
0.625	Remote Similarity	NPD5416	Discontinued
0.625	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD5850	Phase 3
0.6245	Remote Similarity	NPD7568	Phase 1
0.6244	Remote Similarity	NPD5849	Approved
0.624	Remote Similarity	NPD5022	Discontinued
0.624	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6475	Phase 2
0.623	Remote Similarity	NPD3986	Discontinued
0.6229	Remote Similarity	NPD4429	Discontinued
0.6227	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7694	Discontinued
0.6224	Remote Similarity	NPD8430	Approved
0.6223	Remote Similarity	NPD7225	Discontinued
0.6219	Remote Similarity	NPD3845	Phase 1
0.6218	Remote Similarity	NPD7556	Discontinued
0.6218	Remote Similarity	NPD4923	Phase 1
0.6215	Remote Similarity	NPD5471	Phase 3
0.6215	Remote Similarity	NPD7996	Phase 2
0.6214	Remote Similarity	NPD7688	Phase 1
0.6214	Remote Similarity	NPD1505	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