NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	289.22
Volume:	340.26
LogP:	4.453
LogD:	2.701
LogS:	-4.777
# Rotatable Bonds:	12
TPSA:	40.13
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.309
Synthetic Accessibility Score:	3.817
Fsp3:	0.632
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:	-4.486
MDCK Permeability:	2.916630546678789e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.129
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	100.3276596069336%
Volume Distribution (VD):	0.533
Pgp-substrate:	0.4553831219673157%

ADMET: Metabolism

CYP1A2-inhibitor:	0.433
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.461
CYP2C9-inhibitor:	0.824
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	2.39
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.543
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.154
Skin Sensitization:	0.968
Carcinogencity:	0.61
Eye Corrosion:	0.979
Eye Irritation:	0.959
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC477983

Natural Product ID:	NPC477983
*Common Name:**	(E)-Stellettic acid B
IUPAC Name:	(2S,7E)-2-methoxy-12-methyloctadeca-7,17-dien-5-ynoic acid
Synonyms:
Standard InCHIKey:	KHBWVVURFCWYNT-QZEVDHHRSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-4-5-6-12-15-18(2)16-13-10-8-7-9-11-14-17-19(23-3)20(21)22/h4,7-8,18-19H,1,5-6,10,12-17H2,2-3H3,(H,21,22)/b8-7+/t18?,19-/m0/s1
SMILES:	CC(CCCCC=C)CCC/C=C/C#CCC[C@@H](C(=O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11088509
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO33189	Stelletta sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479342]
NPO33189	Stelletta sp.	Species	Ancorinidae	Eukaryota	n.a.	(20 m depth) off Ullung Island, Korea	2001-OCT	PMID[12662102]
NPO33189	Stelletta sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713419]
NPO33189	Stelletta sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762820]
NPO33189	Stelletta sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23465061]
NPO33189	Stelletta sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31646862]
NPO33189	Stelletta sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946745]
NPO33189	Stelletta sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9296951]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30	ug/ml	PMID[12662102]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30	ug/ml	PMID[12662102]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	29.5	ug/ml	PMID[12662102]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30	ug/ml	PMID[12662102]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30	ug/ml	PMID[12662102]

☑ 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 NPC477983 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	174
0.1-0.2	1699
0.2-0.3	8975
0.3-0.4	16858
0.4-0.5	9070
0.5-0.6	5198
0.6-0.7	671
0.7-0.8	42
0.8-0.85	4
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477981
0.9545	High Similarity	NPC477980
0.9429	High Similarity	NPC470899
0.9242	High Similarity	NPC477982
0.8429	Intermediate Similarity	NPC273508
0.8429	Intermediate Similarity	NPC209327
0.8182	Intermediate Similarity	NPC200446
0.8182	Intermediate Similarity	NPC329819
0.8052	Intermediate Similarity	NPC209995
0.7922	Intermediate Similarity	NPC469495
0.7727	Intermediate Similarity	NPC477984
0.7692	Intermediate Similarity	NPC11796
0.7692	Intermediate Similarity	NPC218817
0.7558	Intermediate Similarity	NPC329906
0.7532	Intermediate Similarity	NPC81052
0.75	Intermediate Similarity	NPC476655
0.75	Intermediate Similarity	NPC476657
0.75	Intermediate Similarity	NPC476654
0.7429	Intermediate Similarity	NPC321919
0.7429	Intermediate Similarity	NPC81896
0.7403	Intermediate Similarity	NPC160540
0.7397	Intermediate Similarity	NPC476659
0.7397	Intermediate Similarity	NPC476656
0.7324	Intermediate Similarity	NPC64971
0.7324	Intermediate Similarity	NPC321838
0.7297	Intermediate Similarity	NPC148192
0.7297	Intermediate Similarity	NPC127091
0.7297	Intermediate Similarity	NPC104537
0.7297	Intermediate Similarity	NPC22101
0.7297	Intermediate Similarity	NPC271921
0.7297	Intermediate Similarity	NPC330426
0.7286	Intermediate Similarity	NPC473866
0.7284	Intermediate Similarity	NPC103634
0.7246	Intermediate Similarity	NPC323436
0.72	Intermediate Similarity	NPC48218
0.72	Intermediate Similarity	NPC324981
0.72	Intermediate Similarity	NPC141481
0.72	Intermediate Similarity	NPC473559
0.7179	Intermediate Similarity	NPC104644
0.7123	Intermediate Similarity	NPC34883
0.7123	Intermediate Similarity	NPC476658
0.7121	Intermediate Similarity	NPC48162
0.7083	Intermediate Similarity	NPC174560
0.7083	Intermediate Similarity	NPC125312
0.7083	Intermediate Similarity	NPC328776
0.7083	Intermediate Similarity	NPC201939
0.7083	Intermediate Similarity	NPC320305
0.7073	Intermediate Similarity	NPC233377
0.7067	Intermediate Similarity	NPC473357
0.7067	Intermediate Similarity	NPC475443
0.7067	Intermediate Similarity	NPC193029
0.7067	Intermediate Similarity	NPC473829
0.7059	Intermediate Similarity	NPC137538
0.7059	Intermediate Similarity	NPC475206
0.7042	Intermediate Similarity	NPC329424
0.7042	Intermediate Similarity	NPC278202
0.7015	Intermediate Similarity	NPC236872
0.7013	Intermediate Similarity	NPC42526
0.7013	Intermediate Similarity	NPC318766
0.7013	Intermediate Similarity	NPC476660
0.7	Intermediate Similarity	NPC469514
0.7	Intermediate Similarity	NPC211752
0.7	Intermediate Similarity	NPC121034
0.7	Intermediate Similarity	NPC474527
0.7	Intermediate Similarity	NPC323597
0.7	Intermediate Similarity	NPC471726
0.7	Intermediate Similarity	NPC323498
0.7	Intermediate Similarity	NPC279537
0.697	Remote Similarity	NPC59051
0.6957	Remote Similarity	NPC52264
0.6944	Remote Similarity	NPC243532
0.6941	Remote Similarity	NPC9868
0.6914	Remote Similarity	NPC281296
0.6914	Remote Similarity	NPC40049
0.6905	Remote Similarity	NPC474291
0.6897	Remote Similarity	NPC179659
0.6892	Remote Similarity	NPC328089
0.6892	Remote Similarity	NPC470320
0.6892	Remote Similarity	NPC68343
0.6892	Remote Similarity	NPC226592
0.6889	Remote Similarity	NPC478037
0.6889	Remote Similarity	NPC478036
0.6883	Remote Similarity	NPC473772
0.6883	Remote Similarity	NPC130618
0.6883	Remote Similarity	NPC101622
0.6875	Remote Similarity	NPC199445
0.6857	Remote Similarity	NPC327388
0.6857	Remote Similarity	NPC187777
0.6857	Remote Similarity	NPC179764
0.6842	Remote Similarity	NPC99619
0.6842	Remote Similarity	NPC478100
0.6842	Remote Similarity	NPC26500
0.6835	Remote Similarity	NPC167145
0.6829	Remote Similarity	NPC192006
0.6829	Remote Similarity	NPC121200
0.6824	Remote Similarity	NPC11620
0.6818	Remote Similarity	NPC201046
0.6795	Remote Similarity	NPC473361
0.6795	Remote Similarity	NPC4299
0.6795	Remote Similarity	NPC475310
0.6795	Remote Similarity	NPC329904
0.6786	Remote Similarity	NPC112868
0.6765	Remote Similarity	NPC92114
0.6757	Remote Similarity	NPC54925
0.6757	Remote Similarity	NPC29697
0.6753	Remote Similarity	NPC476614
0.675	Remote Similarity	NPC474321
0.675	Remote Similarity	NPC472966
0.675	Remote Similarity	NPC330016
0.6747	Remote Similarity	NPC471537
0.6744	Remote Similarity	NPC70424
0.6744	Remote Similarity	NPC243618
0.6744	Remote Similarity	NPC474776
0.6744	Remote Similarity	NPC72464
0.6716	Remote Similarity	NPC301482
0.6714	Remote Similarity	NPC473863
0.6714	Remote Similarity	NPC54766
0.6714	Remote Similarity	NPC474672
0.6714	Remote Similarity	NPC45626
0.6714	Remote Similarity	NPC274290
0.6712	Remote Similarity	NPC327112
0.6712	Remote Similarity	NPC328311
0.6711	Remote Similarity	NPC478101
0.6711	Remote Similarity	NPC83965
0.6709	Remote Similarity	NPC67076
0.6709	Remote Similarity	NPC319163
0.6709	Remote Similarity	NPC472254
0.6709	Remote Similarity	NPC126061
0.6706	Remote Similarity	NPC477487
0.6705	Remote Similarity	NPC45409
0.6705	Remote Similarity	NPC248602
0.6667	Remote Similarity	NPC199557
0.6667	Remote Similarity	NPC137033
0.6667	Remote Similarity	NPC471399
0.6667	Remote Similarity	NPC158388
0.6667	Remote Similarity	NPC313670
0.6667	Remote Similarity	NPC91495
0.6667	Remote Similarity	NPC478004
0.6667	Remote Similarity	NPC217725
0.6667	Remote Similarity	NPC478003
0.6667	Remote Similarity	NPC113639
0.6667	Remote Similarity	NPC329852
0.6667	Remote Similarity	NPC329656
0.663	Remote Similarity	NPC121825
0.6628	Remote Similarity	NPC16488
0.6628	Remote Similarity	NPC161045
0.6628	Remote Similarity	NPC49208
0.6627	Remote Similarity	NPC27949
0.6627	Remote Similarity	NPC260814
0.6627	Remote Similarity	NPC127526
0.6627	Remote Similarity	NPC3852
0.6627	Remote Similarity	NPC323249
0.6627	Remote Similarity	NPC39547
0.6625	Remote Similarity	NPC470237
0.6625	Remote Similarity	NPC238425
0.6625	Remote Similarity	NPC472018
0.6625	Remote Similarity	NPC474543
0.6623	Remote Similarity	NPC478097
0.6623	Remote Similarity	NPC25298
0.6622	Remote Similarity	NPC325929
0.6622	Remote Similarity	NPC475984
0.6622	Remote Similarity	NPC66460
0.6622	Remote Similarity	NPC271282
0.662	Remote Similarity	NPC473865
0.662	Remote Similarity	NPC477201
0.662	Remote Similarity	NPC474643
0.6618	Remote Similarity	NPC284212
0.6618	Remote Similarity	NPC28205
0.6593	Remote Similarity	NPC208839
0.6591	Remote Similarity	NPC472009
0.6591	Remote Similarity	NPC477994
0.6591	Remote Similarity	NPC202394
0.6591	Remote Similarity	NPC477993
0.6591	Remote Similarity	NPC164393
0.6591	Remote Similarity	NPC469483
0.6588	Remote Similarity	NPC150502
0.6588	Remote Similarity	NPC47031
0.6588	Remote Similarity	NPC474894
0.6588	Remote Similarity	NPC88735
0.6585	Remote Similarity	NPC474447
0.6585	Remote Similarity	NPC239127
0.6582	Remote Similarity	NPC472017
0.6579	Remote Similarity	NPC255863
0.6579	Remote Similarity	NPC296436
0.6579	Remote Similarity	NPC326268
0.6579	Remote Similarity	NPC136164
0.6579	Remote Similarity	NPC318420
0.6579	Remote Similarity	NPC176215
0.6579	Remote Similarity	NPC245947
0.6575	Remote Similarity	NPC329249
0.6571	Remote Similarity	NPC85813
0.6571	Remote Similarity	NPC6095
0.6571	Remote Similarity	NPC281972
0.6571	Remote Similarity	NPC32467
0.6571	Remote Similarity	NPC424
0.6571	Remote Similarity	NPC290563
0.6571	Remote Similarity	NPC25417
0.6571	Remote Similarity	NPC261831
0.6571	Remote Similarity	NPC88966
0.6571	Remote Similarity	NPC154245

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 NPC477983 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	2380
0.2-0.3	4108
0.3-0.4	1729
0.4-0.5	577
0.5-0.6	168
0.6-0.7	34
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
0.791	Intermediate Similarity	NPD6109	Phase 1
0.7606	Intermediate Similarity	NPD3197	Phase 1
0.7024	Intermediate Similarity	NPD5332	Approved
0.7024	Intermediate Similarity	NPD5331	Approved
0.6829	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5369	Approved
0.6712	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5368	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4822	Approved
0.6628	Remote Similarity	NPD5362	Discontinued
0.6628	Remote Similarity	NPD7154	Phase 3
0.6627	Remote Similarity	NPD4268	Approved
0.6627	Remote Similarity	NPD4271	Approved
0.6593	Remote Similarity	NPD7983	Approved
0.6571	Remote Similarity	NPD4266	Approved
0.6571	Remote Similarity	NPD3196	Approved
0.6571	Remote Similarity	NPD3195	Phase 2
0.6571	Remote Similarity	NPD3194	Approved
0.6512	Remote Similarity	NPD4269	Approved
0.6512	Remote Similarity	NPD4270	Approved
0.6484	Remote Similarity	NPD46	Approved
0.6484	Remote Similarity	NPD6698	Approved
0.6471	Remote Similarity	NPD4252	Approved
0.6437	Remote Similarity	NPD6110	Phase 1
0.6429	Remote Similarity	NPD3172	Approved
0.6418	Remote Similarity	NPD5343	Approved
0.6404	Remote Similarity	NPD5786	Approved
0.6395	Remote Similarity	NPD4790	Discontinued
0.6364	Remote Similarity	NPD39	Approved
0.6364	Remote Similarity	NPD4222	Approved
0.6324	Remote Similarity	NPD3173	Approved
0.6304	Remote Similarity	NPD7838	Discovery
0.6292	Remote Similarity	NPD5363	Approved
0.6279	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6101	Approved
0.6154	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4250	Approved
0.6154	Remote Similarity	NPD4251	Approved
0.6146	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD29	Approved
0.6143	Remote Similarity	NPD28	Approved
0.6129	Remote Similarity	NPD5785	Approved
0.6076	Remote Similarity	NPD7331	Phase 2
0.6071	Remote Similarity	NPD8039	Approved
0.6064	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD5326	Phase 3
0.6047	Remote Similarity	NPD3732	Approved
0.6044	Remote Similarity	NPD4249	Approved
0.6022	Remote Similarity	NPD5370	Suspended
0.6	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.597	Remote Similarity	NPD6097	Approved
0.597	Remote Similarity	NPD6096	Approved
0.593	Remote Similarity	NPD4756	Discovery
0.5922	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6084	Phase 2
0.5918	Remote Similarity	NPD6083	Phase 2
0.5914	Remote Similarity	NPD6672	Approved
0.5914	Remote Similarity	NPD5737	Approved
0.5895	Remote Similarity	NPD7637	Suspended
0.5895	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3174	Discontinued
0.5876	Remote Similarity	NPD5695	Phase 3
0.5875	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6422	Discontinued
0.5859	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6399	Phase 3
0.5823	Remote Similarity	NPD7909	Approved
0.5823	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7839	Suspended
0.5814	Remote Similarity	NPD819	Approved
0.5814	Remote Similarity	NPD818	Approved
0.5794	Remote Similarity	NPD8297	Approved
0.5778	Remote Similarity	NPD5209	Approved
0.5773	Remote Similarity	NPD7748	Approved
0.5761	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7341	Phase 2
0.5729	Remote Similarity	NPD7515	Phase 2
0.5714	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD3198	Approved
0.5714	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD622	Approved
0.57	Remote Similarity	NPD4225	Approved
0.57	Remote Similarity	NPD5696	Approved
0.5699	Remote Similarity	NPD5330	Approved
0.5699	Remote Similarity	NPD7146	Approved
0.5699	Remote Similarity	NPD6098	Approved
0.5699	Remote Similarity	NPD7521	Approved
0.5699	Remote Similarity	NPD5279	Phase 3
0.5699	Remote Similarity	NPD6409	Approved
0.5699	Remote Similarity	NPD7334	Approved
0.5699	Remote Similarity	NPD6684	Approved
0.5694	Remote Similarity	NPD6927	Phase 3
0.5679	Remote Similarity	NPD3704	Approved
0.5676	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3730	Approved
0.5676	Remote Similarity	NPD3728	Approved
0.5673	Remote Similarity	NPD7128	Approved
0.5673	Remote Similarity	NPD6402	Approved
0.5673	Remote Similarity	NPD6675	Approved
0.5673	Remote Similarity	NPD5739	Approved
0.5652	Remote Similarity	NPD4786	Approved
0.5652	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD6933	Approved
0.5619	Remote Similarity	NPD5697	Approved
0.5618	Remote Similarity	NPD6683	Phase 2
0.5612	Remote Similarity	NPD5282	Discontinued
0.5607	Remote Similarity	NPD6883	Approved
0.5607	Remote Similarity	NPD7102	Approved
0.5607	Remote Similarity	NPD7290	Approved
0.5606	Remote Similarity	NPD9635	Discontinued
0.5604	Remote Similarity	NPD3667	Approved
0.56	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7902	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