NPASS Compound

Structure

NPC84038 OpenBabel07101719252D 28 29 0 0 1 0 0 0 0 0999 V2000 14.4408 -0.6395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8413 2.0332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9278 2.4399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6503 2.6210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1187 1.8522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5639 2.2143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2052 2.2589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3729 2.8020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3962 1.6711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2864 2.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4826 2.0779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0954 2.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6736 1.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0090 2.5764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9795 1.0818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7716 0.1037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.1135 1.5818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3704 0.9127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3922 1.1206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7771 -0.0008 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 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 19 1 1 6 0 0 0 19 27 1 0 0 0 0 20 2 1 1 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 24 26 2 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.28
Volume:	431.162
LogP:	8.166
LogD:	4.918
LogS:	-5.142
# Rotatable Bonds:	15
TPSA:	66.74
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	2.674
Fsp3:	0.667
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:	-4.93
MDCK Permeability:	2.3601007342222147e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	96.7737808227539%
Volume Distribution (VD):	4.043
Pgp-substrate:	1.6979482173919678%

ADMET: Metabolism

CYP1A2-inhibitor:	0.203
CYP1A2-substrate:	0.342
CYP2C19-inhibitor:	0.401
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.36
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.177
CYP3A4-substrate:	0.058

ADMET: Excretion

Clearance (CL):	5.895
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.161
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.177
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.935
Carcinogencity:	0.055
Eye Corrosion:	0.007
Eye Irritation:	0.494
Respiratory Toxicity:	0.399

Download Data

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

Natural Product: NPC84038

Natural Product ID:	NPC84038
*Common Name:**	Homoancepsenolide
IUPAC Name:	(2S)-2-methyl-4-[14-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]tetradecyl]-2H-furan-5-one
Synonyms:	Homoancepsenolide
Standard InCHIKey:	WPGYLBYQMCFKCB-PMACEKPBSA-N
Standard InCHI:	InChI=1S/C24H38O4/c1-19-17-21(23(25)27-19)15-13-11-9-7-5-3-4-6-8-10-12-14-16-22-18-20(2)28-24(22)26/h17-20H,3-16H2,1-2H3/t19-,20-/m0/s1
SMILES:	C[C@H]1C=C(CCCCCCCCCCCCCCC2=C[C@H](C)OC2=O)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484441
PubChem CID:	10318257
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO1816	Pterogorgia citrina	Species	Gorgoniidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[7911157]
NPO1816	Pterogorgia citrina	Species	Gorgoniidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[473072]

☑ 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 NPC84038 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	183
0.1-0.2	1741
0.2-0.3	8277
0.3-0.4	17188
0.4-0.5	8473
0.5-0.6	4698
0.6-0.7	1644
0.7-0.8	445
0.8-0.85	39
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC474705
0.9254	High Similarity	NPC218477
0.8857	High Similarity	NPC186531
0.875	High Similarity	NPC469414
0.875	High Similarity	NPC329826
0.8676	High Similarity	NPC248125
0.863	High Similarity	NPC123360
0.8442	Intermediate Similarity	NPC475159
0.8442	Intermediate Similarity	NPC329829
0.8442	Intermediate Similarity	NPC473529
0.8442	Intermediate Similarity	NPC180363
0.8442	Intermediate Similarity	NPC131002
0.8442	Intermediate Similarity	NPC65930
0.8442	Intermediate Similarity	NPC11332
0.8442	Intermediate Similarity	NPC73310
0.8442	Intermediate Similarity	NPC473712
0.8442	Intermediate Similarity	NPC473780
0.8442	Intermediate Similarity	NPC94875
0.8442	Intermediate Similarity	NPC145914
0.84	Intermediate Similarity	NPC128276
0.8356	Intermediate Similarity	NPC140287
0.8356	Intermediate Similarity	NPC476355
0.8333	Intermediate Similarity	NPC475947
0.8333	Intermediate Similarity	NPC253801
0.8333	Intermediate Similarity	NPC144415
0.8312	Intermediate Similarity	NPC471325
0.8286	Intermediate Similarity	NPC203335
0.8267	Intermediate Similarity	NPC57744
0.8228	Intermediate Similarity	NPC156804
0.8228	Intermediate Similarity	NPC163093
0.8219	Intermediate Similarity	NPC144419
0.8205	Intermediate Similarity	NPC173609
0.8125	Intermediate Similarity	NPC25764
0.8125	Intermediate Similarity	NPC120398
0.8125	Intermediate Similarity	NPC283085
0.8125	Intermediate Similarity	NPC39279
0.8125	Intermediate Similarity	NPC110710
0.8125	Intermediate Similarity	NPC9678
0.8125	Intermediate Similarity	NPC319036
0.8125	Intermediate Similarity	NPC82795
0.8125	Intermediate Similarity	NPC322529
0.8125	Intermediate Similarity	NPC329838
0.8125	Intermediate Similarity	NPC470400
0.8125	Intermediate Similarity	NPC292809
0.8125	Intermediate Similarity	NPC475268
0.8125	Intermediate Similarity	NPC477018
0.8125	Intermediate Similarity	NPC66346
0.8125	Intermediate Similarity	NPC329615
0.8125	Intermediate Similarity	NPC471567
0.8125	Intermediate Similarity	NPC473651
0.8125	Intermediate Similarity	NPC477013
0.8125	Intermediate Similarity	NPC107986
0.8125	Intermediate Similarity	NPC103284
0.8125	Intermediate Similarity	NPC202055
0.8125	Intermediate Similarity	NPC132496
0.8125	Intermediate Similarity	NPC1083
0.8125	Intermediate Similarity	NPC223871
0.8125	Intermediate Similarity	NPC473478
0.8125	Intermediate Similarity	NPC286338
0.8125	Intermediate Similarity	NPC473156
0.8125	Intermediate Similarity	NPC473669
0.8125	Intermediate Similarity	NPC100921
0.8125	Intermediate Similarity	NPC231009
0.8125	Intermediate Similarity	NPC473671
0.8125	Intermediate Similarity	NPC39167
0.8125	Intermediate Similarity	NPC235809
0.8125	Intermediate Similarity	NPC477014
0.8125	Intermediate Similarity	NPC77871
0.8108	Intermediate Similarity	NPC474758
0.8088	Intermediate Similarity	NPC151648
0.8082	Intermediate Similarity	NPC163003
0.8052	Intermediate Similarity	NPC178277
0.8028	Intermediate Similarity	NPC472266
0.8026	Intermediate Similarity	NPC68156
0.8026	Intermediate Similarity	NPC97516
0.8026	Intermediate Similarity	NPC10572
0.8025	Intermediate Similarity	NPC477010
0.8025	Intermediate Similarity	NPC210218
0.8025	Intermediate Similarity	NPC282815
0.8025	Intermediate Similarity	NPC232555
0.8025	Intermediate Similarity	NPC107717
0.8025	Intermediate Similarity	NPC62118
0.8025	Intermediate Similarity	NPC103523
0.8025	Intermediate Similarity	NPC204686
0.8025	Intermediate Similarity	NPC134807
0.8025	Intermediate Similarity	NPC231096
0.8025	Intermediate Similarity	NPC241360
0.8025	Intermediate Similarity	NPC112685
0.8025	Intermediate Similarity	NPC473840
0.8025	Intermediate Similarity	NPC219498
0.8025	Intermediate Similarity	NPC134885
0.8025	Intermediate Similarity	NPC475581
0.8025	Intermediate Similarity	NPC134865
0.8025	Intermediate Similarity	NPC142117
0.8025	Intermediate Similarity	NPC477015
0.8025	Intermediate Similarity	NPC171174
0.8025	Intermediate Similarity	NPC240695
0.8025	Intermediate Similarity	NPC279267
0.8025	Intermediate Similarity	NPC132940
0.8025	Intermediate Similarity	NPC308412
0.8025	Intermediate Similarity	NPC473687
0.8025	Intermediate Similarity	NPC69082
0.8025	Intermediate Similarity	NPC25703
0.8025	Intermediate Similarity	NPC114694
0.8025	Intermediate Similarity	NPC219652
0.8025	Intermediate Similarity	NPC309211
0.8025	Intermediate Similarity	NPC293136
0.7975	Intermediate Similarity	NPC35556
0.7945	Intermediate Similarity	NPC469660
0.7945	Intermediate Similarity	NPC67183
0.7941	Intermediate Similarity	NPC143857
0.7941	Intermediate Similarity	NPC229252
0.7927	Intermediate Similarity	NPC20533
0.7927	Intermediate Similarity	NPC258068
0.7927	Intermediate Similarity	NPC473995
0.7927	Intermediate Similarity	NPC470401
0.7927	Intermediate Similarity	NPC178215
0.7927	Intermediate Similarity	NPC154097
0.7927	Intermediate Similarity	NPC473649
0.7927	Intermediate Similarity	NPC476583
0.7927	Intermediate Similarity	NPC159750
0.7927	Intermediate Similarity	NPC477012
0.7922	Intermediate Similarity	NPC299235
0.7922	Intermediate Similarity	NPC93763
0.7922	Intermediate Similarity	NPC108816
0.7901	Intermediate Similarity	NPC182383
0.7895	Intermediate Similarity	NPC27205
0.7867	Intermediate Similarity	NPC117746
0.7867	Intermediate Similarity	NPC294434
0.7867	Intermediate Similarity	NPC15499
0.7867	Intermediate Similarity	NPC259599
0.7848	Intermediate Similarity	NPC42470
0.7831	Intermediate Similarity	NPC320569
0.7831	Intermediate Similarity	NPC242364
0.7831	Intermediate Similarity	NPC320458
0.7831	Intermediate Similarity	NPC81045
0.7831	Intermediate Similarity	NPC21208
0.7831	Intermediate Similarity	NPC233551
0.7831	Intermediate Similarity	NPC234077
0.7831	Intermediate Similarity	NPC61257
0.7831	Intermediate Similarity	NPC169511
0.7831	Intermediate Similarity	NPC133730
0.7831	Intermediate Similarity	NPC40376
0.7831	Intermediate Similarity	NPC151403
0.7831	Intermediate Similarity	NPC280621
0.7831	Intermediate Similarity	NPC171135
0.7831	Intermediate Similarity	NPC261952
0.7831	Intermediate Similarity	NPC287164
0.7831	Intermediate Similarity	NPC20339
0.7831	Intermediate Similarity	NPC39754
0.7831	Intermediate Similarity	NPC191929
0.7831	Intermediate Similarity	NPC48338
0.7831	Intermediate Similarity	NPC172821
0.7831	Intermediate Similarity	NPC100454
0.7831	Intermediate Similarity	NPC89001
0.7831	Intermediate Similarity	NPC473905
0.7831	Intermediate Similarity	NPC274446
0.7821	Intermediate Similarity	NPC471299
0.7821	Intermediate Similarity	NPC270126
0.7805	Intermediate Similarity	NPC284902
0.7805	Intermediate Similarity	NPC469483
0.7805	Intermediate Similarity	NPC47937
0.7792	Intermediate Similarity	NPC41780
0.7792	Intermediate Similarity	NPC476028
0.7792	Intermediate Similarity	NPC187568
0.7792	Intermediate Similarity	NPC171204
0.7792	Intermediate Similarity	NPC476794
0.7792	Intermediate Similarity	NPC141789
0.7792	Intermediate Similarity	NPC470240
0.7778	Intermediate Similarity	NPC194871
0.7763	Intermediate Similarity	NPC244166
0.7746	Intermediate Similarity	NPC133904
0.7738	Intermediate Similarity	NPC42598
0.7738	Intermediate Similarity	NPC81778
0.7738	Intermediate Similarity	NPC477011
0.7738	Intermediate Similarity	NPC91067
0.7738	Intermediate Similarity	NPC477017
0.7738	Intermediate Similarity	NPC318963
0.7738	Intermediate Similarity	NPC473504
0.7738	Intermediate Similarity	NPC20621
0.7738	Intermediate Similarity	NPC139418
0.7738	Intermediate Similarity	NPC14901
0.7738	Intermediate Similarity	NPC477016
0.7738	Intermediate Similarity	NPC40066
0.7738	Intermediate Similarity	NPC280612
0.7738	Intermediate Similarity	NPC93794
0.7738	Intermediate Similarity	NPC130359
0.7733	Intermediate Similarity	NPC295633
0.7733	Intermediate Similarity	NPC58956
0.7733	Intermediate Similarity	NPC269206
0.7722	Intermediate Similarity	NPC474510
0.7722	Intermediate Similarity	NPC281132
0.7714	Intermediate Similarity	NPC44343
0.7714	Intermediate Similarity	NPC68110
0.7714	Intermediate Similarity	NPC179087
0.7714	Intermediate Similarity	NPC210303
0.7711	Intermediate Similarity	NPC475703
0.7692	Intermediate Similarity	NPC471220
0.7683	Intermediate Similarity	NPC215364
0.7681	Intermediate Similarity	NPC79756

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 NPC84038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2444
0.2-0.3	4097
0.3-0.4	1753
0.4-0.5	509
0.5-0.6	143
0.6-0.7	38
0.7-0.8	3
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
0.7531	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6927	Phase 3
0.7108	Intermediate Similarity	NPD5209	Approved
0.7089	Intermediate Similarity	NPD8039	Approved
0.6914	Remote Similarity	NPD4756	Discovery
0.6866	Remote Similarity	NPD28	Approved
0.6866	Remote Similarity	NPD29	Approved
0.686	Remote Similarity	NPD1694	Approved
0.6854	Remote Similarity	NPD5785	Approved
0.6854	Remote Similarity	NPD6698	Approved
0.6854	Remote Similarity	NPD46	Approved
0.6824	Remote Similarity	NPD7154	Phase 3
0.6824	Remote Similarity	NPD5362	Discontinued
0.6711	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3197	Phase 1
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3195	Phase 2
0.6571	Remote Similarity	NPD3196	Approved
0.6571	Remote Similarity	NPD4266	Approved
0.6571	Remote Similarity	NPD3194	Approved
0.6559	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1695	Approved
0.6486	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3172	Approved
0.6418	Remote Similarity	NPD5343	Approved
0.6404	Remote Similarity	NPD7146	Approved
0.6404	Remote Similarity	NPD7521	Approved
0.6404	Remote Similarity	NPD7334	Approved
0.6404	Remote Similarity	NPD6409	Approved
0.6404	Remote Similarity	NPD5330	Approved
0.6404	Remote Similarity	NPD6684	Approved
0.64	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6686	Approved
0.6322	Remote Similarity	NPD6435	Approved
0.6322	Remote Similarity	NPD4270	Approved
0.6322	Remote Similarity	NPD4269	Approved
0.6316	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7838	Discovery
0.6279	Remote Similarity	NPD4252	Approved
0.6264	Remote Similarity	NPD6672	Approved
0.6264	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD5331	Approved
0.6235	Remote Similarity	NPD4271	Approved
0.6235	Remote Similarity	NPD4268	Approved
0.6222	Remote Similarity	NPD5786	Approved
0.6212	Remote Similarity	NPD2699	Approved
0.6207	Remote Similarity	NPD4790	Discontinued
0.6207	Remote Similarity	NPD5369	Approved
0.6203	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD4250	Approved
0.6154	Remote Similarity	NPD4251	Approved
0.6122	Remote Similarity	NPD7640	Approved
0.6122	Remote Similarity	NPD7639	Approved
0.6119	Remote Similarity	NPD3174	Discontinued
0.6092	Remote Similarity	NPD5368	Approved
0.6092	Remote Similarity	NPD4820	Approved
0.6092	Remote Similarity	NPD4822	Approved
0.6092	Remote Similarity	NPD4819	Approved
0.6092	Remote Similarity	NPD4821	Approved
0.6076	Remote Similarity	NPD3704	Approved
0.6076	Remote Similarity	NPD7331	Phase 2
0.6064	Remote Similarity	NPD7983	Approved
0.6064	Remote Similarity	NPD5693	Phase 1
0.6058	Remote Similarity	NPD6371	Approved
0.6044	Remote Similarity	NPD6422	Discontinued
0.6044	Remote Similarity	NPD4249	Approved
0.6026	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.602	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4225	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.5974	Remote Similarity	NPD3205	Discontinued
0.597	Remote Similarity	NPD6097	Approved
0.597	Remote Similarity	NPD6096	Approved
0.5943	Remote Similarity	NPD6053	Discontinued
0.5942	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD2258	Approved
0.5941	Remote Similarity	NPD2259	Approved
0.5938	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7900	Approved
0.5938	Remote Similarity	NPD7748	Approved
0.5905	Remote Similarity	NPD2067	Discontinued
0.5882	Remote Similarity	NPD1452	Discontinued
0.5876	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD3173	Approved
0.5851	Remote Similarity	NPD6904	Approved
0.5851	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5370	Suspended
0.5851	Remote Similarity	NPD6080	Approved
0.5851	Remote Similarity	NPD6673	Approved
0.5851	Remote Similarity	NPD6051	Approved
0.5851	Remote Similarity	NPD6101	Approved
0.5833	Remote Similarity	NPD6399	Phase 3
0.5816	Remote Similarity	NPD7839	Suspended
0.5789	Remote Similarity	NPD6109	Phase 1
0.5784	Remote Similarity	NPD6647	Phase 2
0.5758	Remote Similarity	NPD6084	Phase 2
0.5758	Remote Similarity	NPD7902	Approved
0.5758	Remote Similarity	NPD6083	Phase 2
0.5729	Remote Similarity	NPD6411	Approved
0.5729	Remote Similarity	NPD7515	Phase 2
0.5729	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6050	Approved
0.5727	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD5695	Phase 3
0.5714	Remote Similarity	NPD622	Approved
0.5701	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3728	Approved
0.5676	Remote Similarity	NPD3730	Approved
0.5658	Remote Similarity	NPD8779	Phase 3
0.5644	Remote Similarity	NPD6648	Approved
0.5638	Remote Similarity	NPD3573	Approved
0.5625	Remote Similarity	NPD5207	Approved
0.5625	Remote Similarity	NPD5692	Phase 3
0.5619	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD5282	Discontinued
0.56	Remote Similarity	NPD4627	Clinical (unspecified phase)

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