NPASS Compound

Structure

NPC3214 OpenBabel07101718282D 60 67 0 0 0 0 0 0 0 0999 V2000 8.0077 -1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6476 -3.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4745 2.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9859 -1.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6257 -3.3567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4691 2.1188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3604 -1.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0514 -1.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6556 0.2917 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 2.9032 2.5097 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 2.0897 0.6826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3386 -2.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0678 1.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2949 -2.6136 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 3.0842 0.7872 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 3.4910 1.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0568 1.3098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6501 0.3963 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 1.9087 2.4052 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 1.5019 1.4917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 0.9962 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 3.6720 -0.0219 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 4.6665 0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4855 1.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -0.8309 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.2730 -2.8215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0514 1.4143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2379 -0.4128 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 1.3209 3.2142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8922 2.7188 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 0.7286 2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6682 3.0052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8894 1.6084 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 0.5074 1.3871 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 -0.0804 2.1961 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 28 1 0 0 0 0 13 23 2 0 0 0 0 13 29 1 0 0 0 0 14 24 2 0 0 0 0 14 30 1 0 0 0 0 15 21 2 0 0 0 0 15 31 1 0 0 0 0 16 22 2 0 0 0 0 16 32 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 28 2 0 0 0 0 26 44 1 0 0 0 0 27 45 1 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 32 2 0 0 0 0 30 48 1 0 0 0 0 31 57 1 0 0 0 0 32 58 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 49 2 0 0 0 0 40 50 2 0 0 0 0 51 59 1 0 0 0 0 52 59 2 0 0 0 0 53 59 2 0 0 0 0 54 60 1 0 0 0 0 55 60 2 0 0 0 0 56 60 2 0 0 0 0 57 59 1 0 0 0 0 58 60 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	857.07
Volume:	776.664
LogP:	4.641
LogD:	1.58
LogS:	-3.856
# Rotatable Bonds:	9
TPSA:	307.88
# H-Bond Aceptor:	18
# H-Bond Donor:	9
# Rings:	8
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.038
Synthetic Accessibility Score:	4.048
Fsp3:	0.05
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	3

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.577
MDCK Permeability:	6.921244676050264e-06
Pgp-inhibitor:	0.139
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):	105.6221923828125%
Volume Distribution (VD):	-0.404
Pgp-substrate:	0.8168710470199585%

ADMET: Metabolism

CYP1A2-inhibitor:	0.826
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.165
CYP2C19-substrate:	0.031
CYP2C9-inhibitor:	0.787
CYP2C9-substrate:	0.542
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	1.835
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.789
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.468
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.914
Carcinogencity:	0.869
Eye Corrosion:	0.003
Eye Irritation:	0.924
Respiratory Toxicity:	0.058

Download Data

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

Natural Product: NPC3214

Natural Product ID:	NPC3214
*Common Name:**	Baculiferin D
IUPAC Name:	n.a.
Synonyms:	Baculiferin D
Standard InCHIKey:	DAEAGHNSYXAPRR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C40H27NO17S2/c42-20-5-1-17(2-6-20)9-10-41-37-33(18-3-7-25(43)27(45)11-18)39(49)23-13-29(47)31(57-59(51,52)53)15-21(23)35(37)36-22-16-32(58-60(54,55)56)30(48)14-24(22)40(50)34(38(36)41)19-4-8-26(44)28(46)12-19/h1-8,11-16,42-48H,9-10H2,(H,51,52,53)(H,54,55,56)
SMILES:	c1cc(ccc1CCn1c2=C(c3ccc(c(c3)O)O)C(=O)c3cc(c(cc3-c2c2-c3cc(c(cc3C(=O)C(=c12)c1ccc(c(c1)O)O)O)OS(=O)(=O)O)OS(=O)(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1214281
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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	12.5	ug.mL-1	PMID[525279]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[525279]

☑ 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 NPC3214 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	431
0.1-0.2	2314
0.2-0.3	10698
0.3-0.4	6439
0.4-0.5	12926
0.5-0.6	8740
0.6-0.7	1085
0.7-0.8	52
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC13599
1.0	High Similarity	NPC298840
1.0	High Similarity	NPC268393
1.0	High Similarity	NPC191088
1.0	High Similarity	NPC303384
0.9896	High Similarity	NPC190401
0.9896	High Similarity	NPC239763
0.9688	High Similarity	NPC124086
0.9497	High Similarity	NPC121069
0.9296	High Similarity	NPC246658
0.7677	Intermediate Similarity	NPC256935
0.7426	Intermediate Similarity	NPC271792
0.722	Intermediate Similarity	NPC73555
0.7207	Intermediate Similarity	NPC146976
0.7203	Intermediate Similarity	NPC15406
0.7202	Intermediate Similarity	NPC129897
0.7191	Intermediate Similarity	NPC210296
0.717	Intermediate Similarity	NPC146724
0.7162	Intermediate Similarity	NPC236668
0.715	Intermediate Similarity	NPC472284
0.7119	Intermediate Similarity	NPC318068
0.71	Intermediate Similarity	NPC24019
0.7095	Intermediate Similarity	NPC77878
0.7095	Intermediate Similarity	NPC302807
0.7082	Intermediate Similarity	NPC22481
0.7075	Intermediate Similarity	NPC471448
0.7061	Intermediate Similarity	NPC210434
0.7059	Intermediate Similarity	NPC61038
0.7048	Intermediate Similarity	NPC276657
0.7027	Intermediate Similarity	NPC470020
0.7026	Intermediate Similarity	NPC278525
0.7025	Intermediate Similarity	NPC183537
0.7023	Intermediate Similarity	NPC473814
0.7023	Intermediate Similarity	NPC78767
0.7009	Intermediate Similarity	NPC93390
0.7	Intermediate Similarity	NPC175602
0.6995	Remote Similarity	NPC56170
0.6992	Remote Similarity	NPC182907
0.6992	Remote Similarity	NPC189903
0.6983	Remote Similarity	NPC246381
0.6979	Remote Similarity	NPC253675
0.6967	Remote Similarity	NPC206186
0.6958	Remote Similarity	NPC208522
0.6955	Remote Similarity	NPC181081
0.6952	Remote Similarity	NPC241025
0.6949	Remote Similarity	NPC108342
0.6948	Remote Similarity	NPC132385
0.6936	Remote Similarity	NPC329631
0.6933	Remote Similarity	NPC207866
0.6923	Remote Similarity	NPC472286
0.6923	Remote Similarity	NPC472287
0.6907	Remote Similarity	NPC90875
0.6907	Remote Similarity	NPC208898
0.6904	Remote Similarity	NPC49672
0.69	Remote Similarity	NPC14686
0.6892	Remote Similarity	NPC53344
0.6889	Remote Similarity	NPC110182
0.6888	Remote Similarity	NPC160898
0.6883	Remote Similarity	NPC94842
0.6866	Remote Similarity	NPC74153
0.6858	Remote Similarity	NPC232225
0.6856	Remote Similarity	NPC269270
0.6844	Remote Similarity	NPC9894
0.6844	Remote Similarity	NPC220337
0.6842	Remote Similarity	NPC293151
0.6842	Remote Similarity	NPC27041
0.6822	Remote Similarity	NPC233334
0.682	Remote Similarity	NPC166722
0.6818	Remote Similarity	NPC124313
0.6812	Remote Similarity	NPC204446
0.6809	Remote Similarity	NPC476998
0.6809	Remote Similarity	NPC476996
0.6806	Remote Similarity	NPC473821
0.6805	Remote Similarity	NPC207283
0.6805	Remote Similarity	NPC84164
0.6797	Remote Similarity	NPC253314
0.6794	Remote Similarity	NPC164340
0.6792	Remote Similarity	NPC295158
0.6786	Remote Similarity	NPC207873
0.6786	Remote Similarity	NPC100573
0.678	Remote Similarity	NPC475596
0.678	Remote Similarity	NPC316841
0.678	Remote Similarity	NPC316065
0.678	Remote Similarity	NPC289905
0.678	Remote Similarity	NPC475303
0.6778	Remote Similarity	NPC476995
0.6777	Remote Similarity	NPC475648
0.6776	Remote Similarity	NPC51854
0.6766	Remote Similarity	NPC476997
0.6766	Remote Similarity	NPC476994
0.6761	Remote Similarity	NPC472588
0.6754	Remote Similarity	NPC237740
0.6753	Remote Similarity	NPC469439
0.6752	Remote Similarity	NPC214980
0.6751	Remote Similarity	NPC30456
0.674	Remote Similarity	NPC112206
0.674	Remote Similarity	NPC202605
0.674	Remote Similarity	NPC219087
0.6738	Remote Similarity	NPC51388
0.6735	Remote Similarity	NPC9729
0.6735	Remote Similarity	NPC270515
0.6725	Remote Similarity	NPC322064
0.6722	Remote Similarity	NPC41501
0.6718	Remote Similarity	NPC279589
0.6711	Remote Similarity	NPC171787
0.6709	Remote Similarity	NPC474701
0.6707	Remote Similarity	NPC472589
0.6698	Remote Similarity	NPC183805
0.6696	Remote Similarity	NPC23294
0.6695	Remote Similarity	NPC475406
0.6695	Remote Similarity	NPC220851
0.6695	Remote Similarity	NPC16352
0.6695	Remote Similarity	NPC127720
0.6695	Remote Similarity	NPC127026
0.6695	Remote Similarity	NPC118121
0.6693	Remote Similarity	NPC89549
0.6693	Remote Similarity	NPC191489
0.6692	Remote Similarity	NPC45048
0.6682	Remote Similarity	NPC102008
0.6682	Remote Similarity	NPC17677
0.6681	Remote Similarity	NPC325297
0.6681	Remote Similarity	NPC207686
0.6681	Remote Similarity	NPC54066
0.6681	Remote Similarity	NPC470018
0.6681	Remote Similarity	NPC473506
0.6667	Remote Similarity	NPC283117
0.6667	Remote Similarity	NPC471980
0.6667	Remote Similarity	NPC38959
0.6667	Remote Similarity	NPC478045
0.6667	Remote Similarity	NPC327904
0.6653	Remote Similarity	NPC475631
0.6653	Remote Similarity	NPC475600
0.6653	Remote Similarity	NPC74575
0.6653	Remote Similarity	NPC328186
0.6653	Remote Similarity	NPC477787
0.6653	Remote Similarity	NPC87152
0.6653	Remote Similarity	NPC253482
0.6653	Remote Similarity	NPC211920
0.6653	Remote Similarity	NPC228377
0.6653	Remote Similarity	NPC476110
0.6653	Remote Similarity	NPC122968
0.6653	Remote Similarity	NPC124029
0.6653	Remote Similarity	NPC107123
0.6652	Remote Similarity	NPC303951
0.6652	Remote Similarity	NPC290689
0.6651	Remote Similarity	NPC139763
0.664	Remote Similarity	NPC134637
0.6638	Remote Similarity	NPC48317
0.6638	Remote Similarity	NPC328154
0.6638	Remote Similarity	NPC271215
0.6638	Remote Similarity	NPC149471
0.6637	Remote Similarity	NPC90185
0.6637	Remote Similarity	NPC39679
0.6637	Remote Similarity	NPC86834
0.6637	Remote Similarity	NPC210828
0.6636	Remote Similarity	NPC90229
0.6626	Remote Similarity	NPC475844
0.6625	Remote Similarity	NPC327769
0.6625	Remote Similarity	NPC39370
0.6624	Remote Similarity	NPC471190
0.6624	Remote Similarity	NPC471977
0.6624	Remote Similarity	NPC470486
0.6624	Remote Similarity	NPC475644
0.6623	Remote Similarity	NPC294375
0.662	Remote Similarity	NPC44354
0.6611	Remote Similarity	NPC49547
0.6611	Remote Similarity	NPC132329
0.6606	Remote Similarity	NPC280964
0.6606	Remote Similarity	NPC141915
0.6606	Remote Similarity	NPC114335
0.6598	Remote Similarity	NPC477549
0.6597	Remote Similarity	NPC326363
0.6593	Remote Similarity	NPC270918
0.6592	Remote Similarity	NPC155792
0.6592	Remote Similarity	NPC471489
0.6588	Remote Similarity	NPC315634
0.6588	Remote Similarity	NPC88923
0.6588	Remote Similarity	NPC100734
0.6583	Remote Similarity	NPC172222
0.6583	Remote Similarity	NPC255800
0.6583	Remote Similarity	NPC96584
0.6577	Remote Similarity	NPC5374
0.6577	Remote Similarity	NPC280714
0.6569	Remote Similarity	NPC150698
0.6569	Remote Similarity	NPC96801
0.6569	Remote Similarity	NPC292416
0.6569	Remote Similarity	NPC473689
0.6569	Remote Similarity	NPC201508
0.6568	Remote Similarity	NPC473449
0.6568	Remote Similarity	NPC477902
0.6567	Remote Similarity	NPC84815
0.6567	Remote Similarity	NPC216428
0.6567	Remote Similarity	NPC301368
0.6556	Remote Similarity	NPC35208
0.6555	Remote Similarity	NPC274640
0.6553	Remote Similarity	NPC122463
0.6546	Remote Similarity	NPC473188
0.6542	Remote Similarity	NPC319880
0.6542	Remote Similarity	NPC244839
0.6542	Remote Similarity	NPC320324

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 NPC3214 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	674
0.2-0.3	840
0.3-0.4	1403
0.4-0.5	3314
0.5-0.6	2338
0.6-0.7	316
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
0.7227	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7395	Discontinued
0.6967	Remote Similarity	NPD4948	Discontinued
0.6953	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8091	Phase 3
0.694	Remote Similarity	NPD4845	Discontinued
0.6937	Remote Similarity	NPD6376	Discontinued
0.6936	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5866	Approved
0.6872	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7994	Phase 2
0.6793	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2916	Discontinued
0.678	Remote Similarity	NPD6962	Phase 2
0.6766	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1483	Discontinued
0.6736	Remote Similarity	NPD6716	Phase 1
0.6699	Remote Similarity	NPD2781	Approved
0.6698	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7417	Discontinued
0.6693	Remote Similarity	NPD7708	Approved
0.6682	Remote Similarity	NPD7777	Approved
0.6682	Remote Similarity	NPD53	Approved
0.6682	Remote Similarity	NPD7778	Approved
0.668	Remote Similarity	NPD6456	Discontinued
0.6667	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD8016	Phase 3
0.6636	Remote Similarity	NPD7948	Phase 1
0.6611	Remote Similarity	NPD3746	Discontinued
0.6602	Remote Similarity	NPD2780	Approved
0.6602	Remote Similarity	NPD2782	Approved
0.6593	Remote Similarity	NPD7222	Phase 2
0.6588	Remote Similarity	NPD7803	Approved
0.6583	Remote Similarity	NPD4373	Phase 2
0.6582	Remote Similarity	NPD3259	Approved
0.658	Remote Similarity	NPD8149	Discontinued
0.6578	Remote Similarity	NPD6987	Phase 1
0.6565	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6975	Discontinued
0.6545	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7180	Phase 3
0.6537	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.653	Remote Similarity	NPD3921	Approved
0.653	Remote Similarity	NPD3923	Approved
0.653	Remote Similarity	NPD3922	Approved
0.653	Remote Similarity	NPD3924	Approved
0.6524	Remote Similarity	NPD7878	Phase 2
0.652	Remote Similarity	NPD7452	Approved
0.652	Remote Similarity	NPD7453	Approved
0.652	Remote Similarity	NPD5429	Discontinued
0.6504	Remote Similarity	NPD5901	Discontinued
0.6502	Remote Similarity	NPD5805	Approved
0.6496	Remote Similarity	NPD3258	Approved
0.6494	Remote Similarity	NPD8463	Approved
0.6479	Remote Similarity	NPD3920	Phase 2
0.6473	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4418	Discontinued
0.6471	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6242	Discontinued
0.6463	Remote Similarity	NPD6517	Phase 3
0.6461	Remote Similarity	NPD7853	Phase 2
0.6458	Remote Similarity	NPD4952	Phase 3
0.6456	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5968	Phase 3
0.6452	Remote Similarity	NPD5488	Discontinued
0.6449	Remote Similarity	NPD1643	Phase 3
0.6444	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.644	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6836	Approved
0.6435	Remote Similarity	NPD5914	Approved
0.6432	Remote Similarity	NPD8238	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8396	Approved
0.6429	Remote Similarity	NPD5609	Approved
0.6429	Remote Similarity	NPD5608	Approved
0.6429	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8395	Approved
0.6426	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD3763	Approved
0.6425	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7654	Discontinued
0.6414	Remote Similarity	NPD6995	Phase 1
0.6411	Remote Similarity	NPD7921	Approved
0.641	Remote Similarity	NPD4989	Phase 2
0.6409	Remote Similarity	NPD7925	Phase 2
0.6409	Remote Similarity	NPD7924	Phase 2
0.6402	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8102	Discontinued
0.64	Remote Similarity	NPD484	Approved
0.64	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD1631	Approved
0.6392	Remote Similarity	NPD7955	Approved
0.6392	Remote Similarity	NPD7956	Approved
0.6383	Remote Similarity	NPD3354	Phase 2
0.6382	Remote Similarity	NPD4561	Discontinued
0.6379	Remote Similarity	NPD8093	Discontinued
0.6379	Remote Similarity	NPD3816	Phase 1
0.6379	Remote Similarity	NPD3815	Phase 1
0.6379	Remote Similarity	NPD7069	Discontinued
0.6375	Remote Similarity	NPD4328	Approved
0.6372	Remote Similarity	NPD4511	Phase 1
0.6372	Remote Similarity	NPD5445	Approved
0.6368	Remote Similarity	NPD6733	Discontinued
0.6364	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6790	Phase 1
0.6352	Remote Similarity	NPD8094	Discontinued
0.6338	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3263	Phase 3
0.6332	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4897	Phase 2
0.6325	Remote Similarity	NPD3257	Approved
0.6316	Remote Similarity	NPD7181	Phase 3
0.6316	Remote Similarity	NPD7885	Phase 2
0.6316	Remote Similarity	NPD7886	Phase 2
0.6311	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7922	Phase 1
0.631	Remote Similarity	NPD7588	Discontinued
0.631	Remote Similarity	NPD3809	Discontinued
0.6303	Remote Similarity	NPD5507	Approved
0.6303	Remote Similarity	NPD5506	Approved
0.6296	Remote Similarity	NPD6452	Discontinued
0.6293	Remote Similarity	NPD3229	Phase 2
0.6292	Remote Similarity	NPD7719	Discontinued
0.6292	Remote Similarity	NPD3925	Approved
0.629	Remote Similarity	NPD5928	Phase 1
0.6289	Remote Similarity	NPD5050	Approved
0.6287	Remote Similarity	NPD6974	Phase 3
0.6284	Remote Similarity	NPD7546	Discontinued
0.6283	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6999	Discontinued
0.6282	Remote Similarity	NPD3243	Approved
0.6281	Remote Similarity	NPD7767	Approved
0.6279	Remote Similarity	NPD6159	Phase 2
0.6277	Remote Similarity	NPD4859	Phase 1
0.6277	Remote Similarity	NPD7300	Phase 3
0.6277	Remote Similarity	NPD7302	Phase 3
0.6276	Remote Similarity	NPD8356	Approved
0.6274	Remote Similarity	NPD1573	Approved
0.6274	Remote Similarity	NPD1575	Approved
0.6271	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7658	Phase 2
0.627	Remote Similarity	NPD4885	Approved
0.6267	Remote Similarity	NPD5029	Approved
0.6267	Remote Similarity	NPD5027	Approved
0.6267	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD5031	Approved
0.6266	Remote Similarity	NPD7603	Discontinued
0.6266	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6807	Phase 3
0.6256	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1630	Approved
0.6245	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7301	Phase 3
0.6233	Remote Similarity	NPD5937	Approved
0.6233	Remote Similarity	NPD4941	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD5809	Phase 3
0.6223	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5512	Phase 3
0.622	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4312	Approved
0.6217	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD3962	Phase 2
0.6215	Remote Similarity	NPD3959	Phase 2
0.6208	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7666	Phase 3
0.6207	Remote Similarity	NPD7665	Phase 2
0.6207	Remote Similarity	NPD2420	Approved
0.6207	Remote Similarity	NPD2421	Approved
0.6201	Remote Similarity	NPD7187	Phase 2
0.6197	Remote Similarity	NPD5416	Discontinued
0.6197	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD5850	Phase 3
0.619	Remote Similarity	NPD7568	Phase 1
0.6189	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6189	Remote Similarity	NPD5022	Discontinued
0.6188	Remote Similarity	NPD5849	Approved
0.6181	Remote Similarity	NPD3986	Discontinued
0.6181	Remote Similarity	NPD6475	Phase 2
0.6176	Remote Similarity	NPD4429	Discontinued
0.6173	Remote Similarity	NPD7694	Discontinued
0.6173	Remote Similarity	NPD8430	Approved
0.6171	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7225	Discontinued
0.6167	Remote Similarity	NPD4923	Phase 1
0.6167	Remote Similarity	NPD7556	Discontinued
0.6166	Remote Similarity	NPD7996	Phase 2
0.6165	Remote Similarity	NPD7655	Discontinued
0.6163	Remote Similarity	NPD1505	Phase 2
0.6163	Remote Similarity	NPD7688	Phase 1
0.616	Remote Similarity	NPD5612	Discontinued

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