NPASS Compound

Structure

NPC470436 OpenBabel07101719132D 22 22 0 0 1 0 0 0 0 0999 V2000 -7.8038 -0.8581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6993 0.1364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7857 0.5431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9767 -0.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0632 0.3621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2541 -0.2257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3406 0.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5316 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -3.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 -2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0777 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1180 -1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -4.0287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1180 -1.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 1 0 0 0 16 20 1 1 0 0 0 17 9 1 6 0 0 0 17 22 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.23
Volume:	341.216
LogP:	3.944
LogD:	3.449
LogS:	-4.825
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	4.024
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.767
MDCK Permeability:	6.124259380158037e-05
Pgp-inhibitor:	0.878
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.207
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.862
Plasma Protein Binding (PPB):	86.36668395996094%
Volume Distribution (VD):	0.841
Pgp-substrate:	2.7445480823516846%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.379
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	7.64
Half-life (T1/2):	0.413

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.489
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.41
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.883
Carcinogencity:	0.28
Eye Corrosion:	0.013
Eye Irritation:	0.419
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC470436

Natural Product ID:	NPC470436
*Common Name:**	Seimatopolide B
IUPAC Name:	(2S,5S,6E,8R)-5,8-dihydroxy-2-nonyl-2,3,4,5,8,9-hexahydrooxecin-10-one
Synonyms:	Seimatopolide B
Standard InCHIKey:	XPIVIEHYRXZHSQ-SRXSTOJXSA-N
Standard InCHI:	InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-9-17-13-12-15(19)10-11-16(20)14-18(21)22-17/h10-11,15-17,19-20H,2-9,12-14H2,1H3/b11-10+/t15-,16+,17+/m1/s1
SMILES:	CCCCCCCCC[C@H]1CC[C@H](O)/C=C/[C@@H](CC(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036278
PubChem CID:	57409556
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001796] Oxocins

*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
NPO33344	seimatosporium discosioides	Species	Amphisphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22424300]

☑ 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
EC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	11050.0	nM	PMID[495167]

☑ 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 NPC470436 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	177
0.1-0.2	2014
0.2-0.3	7458
0.3-0.4	18362
0.4-0.5	9047
0.5-0.6	4245
0.6-0.7	1178
0.7-0.8	203
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC470435
0.8615	High Similarity	NPC113293
0.8261	Intermediate Similarity	NPC25298
0.8209	Intermediate Similarity	NPC29697
0.806	Intermediate Similarity	NPC325929
0.806	Intermediate Similarity	NPC271282
0.806	Intermediate Similarity	NPC66460
0.803	Intermediate Similarity	NPC318306
0.8028	Intermediate Similarity	NPC130618
0.8	Intermediate Similarity	NPC26500
0.8	Intermediate Similarity	NPC271921
0.8	Intermediate Similarity	NPC22101
0.8	Intermediate Similarity	NPC330426
0.8	Intermediate Similarity	NPC104537
0.8	Intermediate Similarity	NPC99619
0.8	Intermediate Similarity	NPC127091
0.8	Intermediate Similarity	NPC148192
0.7973	Intermediate Similarity	NPC260396
0.7971	Intermediate Similarity	NPC245947
0.7971	Intermediate Similarity	NPC255863
0.7971	Intermediate Similarity	NPC136164
0.7917	Intermediate Similarity	NPC42526
0.791	Intermediate Similarity	NPC327112
0.7887	Intermediate Similarity	NPC473559
0.7887	Intermediate Similarity	NPC324981
0.7887	Intermediate Similarity	NPC141481
0.7887	Intermediate Similarity	NPC48218
0.7867	Intermediate Similarity	NPC190400
0.7867	Intermediate Similarity	NPC49392
0.7857	Intermediate Similarity	NPC284447
0.7826	Intermediate Similarity	NPC470320
0.7794	Intermediate Similarity	NPC475984
0.7794	Intermediate Similarity	NPC321838
0.7794	Intermediate Similarity	NPC201939
0.7794	Intermediate Similarity	NPC320305
0.7794	Intermediate Similarity	NPC328776
0.7746	Intermediate Similarity	NPC473829
0.7746	Intermediate Similarity	NPC475443
0.7733	Intermediate Similarity	NPC473582
0.7714	Intermediate Similarity	NPC476657
0.7714	Intermediate Similarity	NPC318420
0.7714	Intermediate Similarity	NPC476655
0.7714	Intermediate Similarity	NPC476654
0.7714	Intermediate Similarity	NPC326268
0.7703	Intermediate Similarity	NPC329890
0.7692	Intermediate Similarity	NPC52264
0.7681	Intermediate Similarity	NPC470965
0.7671	Intermediate Similarity	NPC476660
0.7662	Intermediate Similarity	NPC127526
0.7662	Intermediate Similarity	NPC182292
0.7647	Intermediate Similarity	NPC328311
0.7647	Intermediate Similarity	NPC81896
0.7647	Intermediate Similarity	NPC243532
0.7647	Intermediate Similarity	NPC321919
0.7606	Intermediate Similarity	NPC476656
0.7606	Intermediate Similarity	NPC476659
0.76	Intermediate Similarity	NPC326504
0.76	Intermediate Similarity	NPC473489
0.7571	Intermediate Similarity	NPC328089
0.7571	Intermediate Similarity	NPC226592
0.7571	Intermediate Similarity	NPC68343
0.7571	Intermediate Similarity	NPC476658
0.7568	Intermediate Similarity	NPC293114
0.7538	Intermediate Similarity	NPC137538
0.7536	Intermediate Similarity	NPC26810
0.7534	Intermediate Similarity	NPC143396
0.7534	Intermediate Similarity	NPC473772
0.7532	Intermediate Similarity	NPC233071
0.7532	Intermediate Similarity	NPC281296
0.75	Intermediate Similarity	NPC478097
0.75	Intermediate Similarity	NPC322002
0.7467	Intermediate Similarity	NPC284006
0.7467	Intermediate Similarity	NPC185186
0.7467	Intermediate Similarity	NPC327383
0.7467	Intermediate Similarity	NPC329914
0.7467	Intermediate Similarity	NPC144419
0.7436	Intermediate Similarity	NPC121200
0.7436	Intermediate Similarity	NPC39547
0.7436	Intermediate Similarity	NPC323249
0.7436	Intermediate Similarity	NPC248775
0.7436	Intermediate Similarity	NPC318481
0.7436	Intermediate Similarity	NPC27949
0.7436	Intermediate Similarity	NPC260814
0.7432	Intermediate Similarity	NPC4299
0.7432	Intermediate Similarity	NPC476037
0.7429	Intermediate Similarity	NPC54925
0.7407	Intermediate Similarity	NPC69469
0.7403	Intermediate Similarity	NPC188860
0.7403	Intermediate Similarity	NPC16279
0.7403	Intermediate Similarity	NPC205615
0.7403	Intermediate Similarity	NPC256640
0.7397	Intermediate Similarity	NPC209327
0.7397	Intermediate Similarity	NPC273508
0.7368	Intermediate Similarity	NPC474321
0.7368	Intermediate Similarity	NPC227396
0.7361	Intermediate Similarity	NPC146811
0.7342	Intermediate Similarity	NPC470148
0.7342	Intermediate Similarity	NPC263574
0.7342	Intermediate Similarity	NPC180725
0.7342	Intermediate Similarity	NPC201225
0.7342	Intermediate Similarity	NPC470149
0.7342	Intermediate Similarity	NPC1180
0.7342	Intermediate Similarity	NPC469747
0.7333	Intermediate Similarity	NPC320119
0.7324	Intermediate Similarity	NPC475221
0.7317	Intermediate Similarity	NPC158756
0.7308	Intermediate Similarity	NPC474278
0.7297	Intermediate Similarity	NPC236208
0.7297	Intermediate Similarity	NPC101622
0.7286	Intermediate Similarity	NPC477829
0.7284	Intermediate Similarity	NPC474252
0.7273	Intermediate Similarity	NPC327041
0.7273	Intermediate Similarity	NPC199445
0.7273	Intermediate Similarity	NPC285840
0.7273	Intermediate Similarity	NPC473948
0.7262	Intermediate Similarity	NPC86005
0.7262	Intermediate Similarity	NPC477959
0.726	Intermediate Similarity	NPC49863
0.726	Intermediate Similarity	NPC478100
0.725	Intermediate Similarity	NPC470147
0.725	Intermediate Similarity	NPC133226
0.7246	Intermediate Similarity	NPC322186
0.7246	Intermediate Similarity	NPC329249
0.7246	Intermediate Similarity	NPC97570
0.7246	Intermediate Similarity	NPC474267
0.7237	Intermediate Similarity	NPC326024
0.7237	Intermediate Similarity	NPC325627
0.7237	Intermediate Similarity	NPC477085
0.7229	Intermediate Similarity	NPC470755
0.7229	Intermediate Similarity	NPC261380
0.7222	Intermediate Similarity	NPC323045
0.7222	Intermediate Similarity	NPC317881
0.7222	Intermediate Similarity	NPC478099
0.7222	Intermediate Similarity	NPC478098
0.7215	Intermediate Similarity	NPC218817
0.7215	Intermediate Similarity	NPC473471
0.7215	Intermediate Similarity	NPC11796
0.7206	Intermediate Similarity	NPC323597
0.7206	Intermediate Similarity	NPC323498
0.7206	Intermediate Similarity	NPC323436
0.7206	Intermediate Similarity	NPC193975
0.7206	Intermediate Similarity	NPC44542
0.7206	Intermediate Similarity	NPC211752
0.72	Intermediate Similarity	NPC476012
0.7195	Intermediate Similarity	NPC284472
0.7195	Intermediate Similarity	NPC286770
0.7195	Intermediate Similarity	NPC229799
0.7179	Intermediate Similarity	NPC469514
0.7179	Intermediate Similarity	NPC474447
0.7179	Intermediate Similarity	NPC279537
0.7164	Intermediate Similarity	NPC223677
0.7164	Intermediate Similarity	NPC10316
0.7164	Intermediate Similarity	NPC128061
0.7164	Intermediate Similarity	NPC28779
0.7164	Intermediate Similarity	NPC200845
0.7162	Intermediate Similarity	NPC63873
0.716	Intermediate Similarity	NPC316844
0.716	Intermediate Similarity	NPC112868
0.716	Intermediate Similarity	NPC88735
0.716	Intermediate Similarity	NPC47031
0.7143	Intermediate Similarity	NPC474551
0.7143	Intermediate Similarity	NPC471278
0.7143	Intermediate Similarity	NPC469910
0.7125	Intermediate Similarity	NPC321728
0.7125	Intermediate Similarity	NPC475210
0.7123	Intermediate Similarity	NPC83965
0.7123	Intermediate Similarity	NPC328653
0.7123	Intermediate Similarity	NPC478101
0.7121	Intermediate Similarity	NPC474496
0.7105	Intermediate Similarity	NPC472254
0.7105	Intermediate Similarity	NPC477087
0.7105	Intermediate Similarity	NPC477086
0.7105	Intermediate Similarity	NPC126061
0.7089	Intermediate Similarity	NPC176329
0.7089	Intermediate Similarity	NPC474818
0.7089	Intermediate Similarity	NPC51809
0.7089	Intermediate Similarity	NPC49302
0.7089	Intermediate Similarity	NPC125365
0.7089	Intermediate Similarity	NPC474026
0.7073	Intermediate Similarity	NPC7414
0.7073	Intermediate Similarity	NPC475046
0.7073	Intermediate Similarity	NPC474959
0.7073	Intermediate Similarity	NPC85772
0.7073	Intermediate Similarity	NPC310450
0.7073	Intermediate Similarity	NPC11383
0.7067	Intermediate Similarity	NPC317583
0.7067	Intermediate Similarity	NPC475004
0.7059	Intermediate Similarity	NPC477201
0.7059	Intermediate Similarity	NPC471738
0.7059	Intermediate Similarity	NPC327388
0.7059	Intermediate Similarity	NPC316629
0.7051	Intermediate Similarity	NPC60718
0.7042	Intermediate Similarity	NPC55376
0.7037	Intermediate Similarity	NPC115418
0.7031	Intermediate Similarity	NPC207815
0.7027	Intermediate Similarity	NPC122627
0.7027	Intermediate Similarity	NPC193029
0.7027	Intermediate Similarity	NPC473357
0.7024	Intermediate Similarity	NPC11804
0.7024	Intermediate Similarity	NPC255307

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 NPC470436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	2700
0.2-0.3	3770
0.3-0.4	1873
0.4-0.5	520
0.5-0.6	81
0.6-0.7	55
0.7-0.8	6
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
0.791	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4271	Approved
0.7436	Intermediate Similarity	NPD4268	Approved
0.7324	Intermediate Similarity	NPD3197	Phase 1
0.726	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4821	Approved
0.725	Intermediate Similarity	NPD4819	Approved
0.725	Intermediate Similarity	NPD4820	Approved
0.725	Intermediate Similarity	NPD4822	Approved
0.7195	Intermediate Similarity	NPD7154	Phase 3
0.7126	Intermediate Similarity	NPD7983	Approved
0.7073	Intermediate Similarity	NPD4270	Approved
0.7073	Intermediate Similarity	NPD4269	Approved
0.7059	Intermediate Similarity	NPD4251	Approved
0.7059	Intermediate Similarity	NPD4250	Approved
0.7037	Intermediate Similarity	NPD4252	Approved
0.7015	Intermediate Similarity	NPD3194	Approved
0.7015	Intermediate Similarity	NPD3196	Approved
0.7015	Intermediate Similarity	NPD4266	Approved
0.7015	Intermediate Similarity	NPD3195	Phase 2
0.6941	Remote Similarity	NPD5786	Approved
0.6941	Remote Similarity	NPD4249	Approved
0.6867	Remote Similarity	NPD6435	Approved
0.6866	Remote Similarity	NPD3172	Approved
0.6857	Remote Similarity	NPD6109	Phase 1
0.6854	Remote Similarity	NPD5778	Approved
0.6854	Remote Similarity	NPD5779	Approved
0.6824	Remote Similarity	NPD5363	Approved
0.679	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5362	Discontinued
0.6747	Remote Similarity	NPD5369	Approved
0.6742	Remote Similarity	NPD7637	Suspended
0.6705	Remote Similarity	NPD5370	Suspended
0.663	Remote Similarity	NPD7839	Suspended
0.6629	Remote Similarity	NPD5785	Approved
0.6628	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5368	Approved
0.6615	Remote Similarity	NPD5343	Approved
0.6588	Remote Similarity	NPD5331	Approved
0.6588	Remote Similarity	NPD5332	Approved
0.6567	Remote Similarity	NPD29	Approved
0.6567	Remote Similarity	NPD28	Approved
0.6562	Remote Similarity	NPD39	Approved
0.6556	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4790	Discontinued
0.6517	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6101	Approved
0.6515	Remote Similarity	NPD3173	Approved
0.6444	Remote Similarity	NPD7838	Discovery
0.6444	Remote Similarity	NPD6698	Approved
0.6444	Remote Similarity	NPD46	Approved
0.6406	Remote Similarity	NPD6097	Approved
0.6406	Remote Similarity	NPD6096	Approved
0.6386	Remote Similarity	NPD3732	Approved
0.6374	Remote Similarity	NPD6411	Approved
0.6324	Remote Similarity	NPD6927	Phase 3
0.6308	Remote Similarity	NPD4222	Approved
0.6286	Remote Similarity	NPD3730	Approved
0.6286	Remote Similarity	NPD3728	Approved
0.6265	Remote Similarity	NPD4756	Discovery
0.625	Remote Similarity	NPD5326	Phase 3
0.617	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4225	Approved
0.6136	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD622	Approved
0.6104	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD5209	Approved
0.6061	Remote Similarity	NPD4265	Approved
0.6061	Remote Similarity	NPD3174	Discontinued
0.6053	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD8039	Approved
0.5952	Remote Similarity	NPD818	Approved
0.5952	Remote Similarity	NPD819	Approved
0.5946	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6371	Approved
0.5859	Remote Similarity	NPD5344	Discontinued
0.5773	Remote Similarity	NPD4228	Discovery
0.5773	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7640	Approved
0.5758	Remote Similarity	NPD7639	Approved
0.5745	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6647	Phase 2
0.5732	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD368	Approved
0.5672	Remote Similarity	NPD2699	Approved
0.566	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7638	Approved
0.5652	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6422	Discontinued
0.5631	Remote Similarity	NPD5048	Discontinued
0.5625	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6399	Phase 3
0.5625	Remote Similarity	NPD3704	Approved
0.5619	Remote Similarity	NPD6413	Approved
0.5616	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6648	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