NPASS Compound

Structure

NPC76054 OpenBabel07101718192D 23 26 0 0 1 0 0 0 0 0999 V2000 -2.4109 -0.0210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5849 2.3635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0591 -1.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8142 -1.6370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3350 1.3166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2629 -0.8801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7589 -0.5937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5423 -0.0539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2161 -0.9501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7291 -0.3441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5849 0.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2331 -0.5937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3373 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7589 -0.0210 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7291 0.2654 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2331 -0.0210 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2629 0.2654 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2629 0.8381 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7907 0.5333 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2629 -0.9168 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1764 -1.8667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3373 0.7323 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 13 2 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 13 20 1 0 0 0 0 14 11 1 6 0 0 0 14 17 1 0 0 0 0 15 10 1 6 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 12 1 1 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	3.815
LogD:	4.083
LogS:	-4.497
# Rotatable Bonds:	1
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	6.174
Fsp3:	0.8
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:	-4.624
MDCK Permeability:	1.759157021297142e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.473
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	76.32430267333984%
Volume Distribution (VD):	1.662
Pgp-substrate:	15.402822494506836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.813
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.119
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.624
CYP3A4-substrate:	0.869

ADMET: Excretion

Clearance (CL):	11.317
Half-life (T1/2):	0.231

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.36
Drug-inuced Liver Injury (DILI):	0.614
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.235
Skin Sensitization:	0.038
Carcinogencity:	0.233
Eye Corrosion:	0.019
Eye Irritation:	0.09
Respiratory Toxicity:	0.096

Download Data

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

Natural Product: NPC76054

Natural Product ID:	NPC76054
*Common Name:**	Pachycladin D
IUPAC Name:	n.a.
Synonyms:	Pachycladin D
Standard InCHIKey:	UIIHNSMHUFJCOO-BVMALAMASA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-11(2)14-7-6-12(3)16-15-10-13(4)20(21)9-8-19(5,23-20)18(22-15)17(14)16/h11,14-18,21H,3-4,6-10H2,1-2,5H3/t14-,15-,16-,17-,18-,19-,20+/m1/s1
SMILES:	CC(C)[C@H]1CCC(=C)[C@@H]2[C@H]3CC(=C)[C@@]4(CC[C@](C)([C@@H]([C@H]12)O3)O4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096782
PubChem CID:	46833117
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	red sea soft coral	n.a.	PMID[20420415]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	75000.0	nM	PMID[536681]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	13333341.42	nM	PMID[536681]

☑ 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 NPC76054 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	175
0.1-0.2	1878
0.2-0.3	7120
0.3-0.4	16169
0.4-0.5	8552
0.5-0.6	7519
0.6-0.7	1245
0.7-0.8	37
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8706	High Similarity	NPC8729
0.8228	Intermediate Similarity	NPC329626
0.8072	Intermediate Similarity	NPC103171
0.7952	Intermediate Similarity	NPC77003
0.7875	Intermediate Similarity	NPC36479
0.7805	Intermediate Similarity	NPC264610
0.7778	Intermediate Similarity	NPC293223
0.7765	Intermediate Similarity	NPC5958
0.7586	Intermediate Similarity	NPC471379
0.7586	Intermediate Similarity	NPC196911
0.7586	Intermediate Similarity	NPC119001
0.7529	Intermediate Similarity	NPC118116
0.75	Intermediate Similarity	NPC476701
0.75	Intermediate Similarity	NPC322922
0.75	Intermediate Similarity	NPC475684
0.75	Intermediate Similarity	NPC321812
0.7439	Intermediate Similarity	NPC12696
0.7416	Intermediate Similarity	NPC44538
0.7363	Intermediate Similarity	NPC470817
0.7356	Intermediate Similarity	NPC127917
0.7356	Intermediate Similarity	NPC239308
0.7349	Intermediate Similarity	NPC152017
0.7333	Intermediate Similarity	NPC75443
0.7333	Intermediate Similarity	NPC476723
0.7333	Intermediate Similarity	NPC92370
0.7333	Intermediate Similarity	NPC470260
0.7333	Intermediate Similarity	NPC476724
0.7283	Intermediate Similarity	NPC122057
0.7263	Intermediate Similarity	NPC26307
0.7253	Intermediate Similarity	NPC161560
0.7253	Intermediate Similarity	NPC291875
0.7253	Intermediate Similarity	NPC470819
0.7195	Intermediate Similarity	NPC143576
0.7176	Intermediate Similarity	NPC470944
0.7174	Intermediate Similarity	NPC474323
0.7174	Intermediate Similarity	NPC312471
0.7174	Intermediate Similarity	NPC471378
0.7174	Intermediate Similarity	NPC206614
0.7111	Intermediate Similarity	NPC162071
0.7097	Intermediate Similarity	NPC91251
0.7093	Intermediate Similarity	NPC72755
0.7093	Intermediate Similarity	NPC476367
0.7079	Intermediate Similarity	NPC83702
0.7065	Intermediate Similarity	NPC477917
0.7053	Intermediate Similarity	NPC476720
0.7033	Intermediate Similarity	NPC186148
0.7033	Intermediate Similarity	NPC476948
0.7033	Intermediate Similarity	NPC474832
0.7024	Intermediate Similarity	NPC85831
0.7024	Intermediate Similarity	NPC265921
0.7024	Intermediate Similarity	NPC215215
0.7021	Intermediate Similarity	NPC91654
0.7021	Intermediate Similarity	NPC67398
0.7021	Intermediate Similarity	NPC474792
0.7021	Intermediate Similarity	NPC470187
0.7021	Intermediate Similarity	NPC474835
0.7	Intermediate Similarity	NPC476725
0.6977	Remote Similarity	NPC477089
0.6962	Remote Similarity	NPC250836
0.6961	Remote Similarity	NPC38948
0.6957	Remote Similarity	NPC177629
0.6957	Remote Similarity	NPC58219
0.6947	Remote Similarity	NPC472360
0.6947	Remote Similarity	NPC472416
0.6947	Remote Similarity	NPC189513
0.6941	Remote Similarity	NPC236228
0.6941	Remote Similarity	NPC256720
0.6923	Remote Similarity	NPC311163
0.6915	Remote Similarity	NPC208839
0.6915	Remote Similarity	NPC312805
0.6915	Remote Similarity	NPC302584
0.6907	Remote Similarity	NPC98112
0.6897	Remote Similarity	NPC233295
0.6897	Remote Similarity	NPC17550
0.6893	Remote Similarity	NPC206618
0.6889	Remote Similarity	NPC319238
0.6882	Remote Similarity	NPC92974
0.6882	Remote Similarity	NPC299527
0.6875	Remote Similarity	NPC135224
0.6875	Remote Similarity	NPC473348
0.6875	Remote Similarity	NPC477970
0.6875	Remote Similarity	NPC100892
0.6875	Remote Similarity	NPC477969
0.6875	Remote Similarity	NPC30477
0.6869	Remote Similarity	NPC471112
0.6867	Remote Similarity	NPC306085
0.686	Remote Similarity	NPC474826
0.686	Remote Similarity	NPC477425
0.686	Remote Similarity	NPC477427
0.686	Remote Similarity	NPC477426
0.686	Remote Similarity	NPC476703
0.6854	Remote Similarity	NPC122945
0.6854	Remote Similarity	NPC109938
0.6842	Remote Similarity	NPC296620
0.6837	Remote Similarity	NPC187268
0.6837	Remote Similarity	NPC309493
0.6829	Remote Similarity	NPC16964
0.6829	Remote Similarity	NPC234511
0.6818	Remote Similarity	NPC206062
0.6818	Remote Similarity	NPC474592
0.6818	Remote Similarity	NPC186072
0.6813	Remote Similarity	NPC471494
0.6813	Remote Similarity	NPC470658
0.6809	Remote Similarity	NPC220216
0.6809	Remote Similarity	NPC159876
0.6809	Remote Similarity	NPC474249
0.6809	Remote Similarity	NPC261990
0.6804	Remote Similarity	NPC471765
0.6804	Remote Similarity	NPC211810
0.6804	Remote Similarity	NPC284194
0.6804	Remote Similarity	NPC221801
0.68	Remote Similarity	NPC472815
0.68	Remote Similarity	NPC52585
0.68	Remote Similarity	NPC68630
0.68	Remote Similarity	NPC228049
0.6786	Remote Similarity	NPC476709
0.6782	Remote Similarity	NPC52755
0.6782	Remote Similarity	NPC3852
0.6782	Remote Similarity	NPC181838
0.6782	Remote Similarity	NPC137345
0.6778	Remote Similarity	NPC49208
0.6774	Remote Similarity	NPC309656
0.6774	Remote Similarity	NPC473436
0.6771	Remote Similarity	NPC474338
0.6768	Remote Similarity	NPC272223
0.6765	Remote Similarity	NPC127609
0.6747	Remote Similarity	NPC129630
0.6744	Remote Similarity	NPC107963
0.6742	Remote Similarity	NPC5361
0.6742	Remote Similarity	NPC246621
0.6742	Remote Similarity	NPC15978
0.6739	Remote Similarity	NPC476217
0.6739	Remote Similarity	NPC255143
0.6739	Remote Similarity	NPC472379
0.6739	Remote Similarity	NPC471219
0.6737	Remote Similarity	NPC12172
0.6737	Remote Similarity	NPC124374
0.6737	Remote Similarity	NPC208886
0.6737	Remote Similarity	NPC471747
0.6735	Remote Similarity	NPC473244
0.6735	Remote Similarity	NPC304445
0.6735	Remote Similarity	NPC91197
0.6735	Remote Similarity	NPC125551
0.6735	Remote Similarity	NPC96597
0.6735	Remote Similarity	NPC309503
0.6735	Remote Similarity	NPC239547
0.6735	Remote Similarity	NPC236580
0.6735	Remote Similarity	NPC155319
0.6733	Remote Similarity	NPC120009
0.6731	Remote Similarity	NPC128133
0.6707	Remote Similarity	NPC245795
0.6707	Remote Similarity	NPC266578
0.6705	Remote Similarity	NPC86971
0.6703	Remote Similarity	NPC116613
0.6703	Remote Similarity	NPC474780
0.6703	Remote Similarity	NPC46320
0.6702	Remote Similarity	NPC261320
0.6702	Remote Similarity	NPC473058
0.6702	Remote Similarity	NPC246028
0.6702	Remote Similarity	NPC115607
0.6702	Remote Similarity	NPC249408
0.6702	Remote Similarity	NPC104129
0.6701	Remote Similarity	NPC90014
0.67	Remote Similarity	NPC305085
0.67	Remote Similarity	NPC176406
0.67	Remote Similarity	NPC67296
0.67	Remote Similarity	NPC84042
0.6699	Remote Similarity	NPC476594
0.6667	Remote Similarity	NPC155521
0.6667	Remote Similarity	NPC242419
0.6667	Remote Similarity	NPC216260
0.6667	Remote Similarity	NPC99653
0.6667	Remote Similarity	NPC179746
0.6667	Remote Similarity	NPC235126
0.6667	Remote Similarity	NPC476895
0.6667	Remote Similarity	NPC5358
0.6667	Remote Similarity	NPC81419
0.6667	Remote Similarity	NPC190753
0.6667	Remote Similarity	NPC471796
0.6636	Remote Similarity	NPC293658
0.6636	Remote Similarity	NPC474410
0.6635	Remote Similarity	NPC476513
0.6635	Remote Similarity	NPC473517
0.6635	Remote Similarity	NPC181994
0.6634	Remote Similarity	NPC300399
0.6634	Remote Similarity	NPC471482
0.6634	Remote Similarity	NPC471889
0.6634	Remote Similarity	NPC177701
0.6633	Remote Similarity	NPC165632
0.6633	Remote Similarity	NPC474297
0.6633	Remote Similarity	NPC473964
0.6633	Remote Similarity	NPC284518
0.6633	Remote Similarity	NPC284063
0.6633	Remote Similarity	NPC90583
0.6632	Remote Similarity	NPC209816
0.663	Remote Similarity	NPC290731
0.663	Remote Similarity	NPC47958
0.663	Remote Similarity	NPC149725
0.663	Remote Similarity	NPC304509
0.663	Remote Similarity	NPC298595

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 NPC76054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	2500
0.2-0.3	4168
0.3-0.4	1671
0.4-0.5	453
0.5-0.6	171
0.6-0.7	8
0.7-0.8	0
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
0.6883	Remote Similarity	NPD1145	Discontinued
0.6522	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7524	Approved
0.6458	Remote Similarity	NPD3168	Discontinued
0.6413	Remote Similarity	NPD6695	Phase 3
0.6373	Remote Similarity	NPD5344	Discontinued
0.6275	Remote Similarity	NPD6648	Approved
0.6264	Remote Similarity	NPD6930	Phase 2
0.6264	Remote Similarity	NPD6931	Approved
0.6176	Remote Similarity	NPD4225	Approved
0.6176	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6686	Approved
0.6154	Remote Similarity	NPD6929	Approved
0.6146	Remote Similarity	NPD7750	Discontinued
0.6036	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD6933	Approved
0.6	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD7328	Approved
0.5965	Remote Similarity	NPD7327	Approved
0.5962	Remote Similarity	NPD7640	Approved
0.5962	Remote Similarity	NPD7639	Approved
0.596	Remote Similarity	NPD6698	Approved
0.596	Remote Similarity	NPD46	Approved
0.596	Remote Similarity	NPD7838	Discovery
0.5955	Remote Similarity	NPD1811	Approved
0.5955	Remote Similarity	NPD1810	Approved
0.5955	Remote Similarity	NPD6924	Approved
0.5955	Remote Similarity	NPD6926	Approved
0.5948	Remote Similarity	NPD8033	Approved
0.5938	Remote Similarity	NPD6893	Approved
0.5934	Remote Similarity	NPD5776	Phase 2
0.5934	Remote Similarity	NPD6925	Approved
0.5926	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7514	Phase 3
0.5914	Remote Similarity	NPD7332	Phase 2
0.5914	Remote Similarity	NPD6928	Phase 2
0.5913	Remote Similarity	NPD7516	Approved
0.59	Remote Similarity	NPD7087	Discontinued
0.5876	Remote Similarity	NPD4249	Approved
0.587	Remote Similarity	NPD7145	Approved
0.5865	Remote Similarity	NPD7638	Approved
0.5862	Remote Similarity	NPD8377	Approved
0.5862	Remote Similarity	NPD8294	Approved
0.5859	Remote Similarity	NPD1695	Approved
0.5851	Remote Similarity	NPD6898	Phase 1
0.5833	Remote Similarity	NPD5357	Phase 1
0.5824	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4251	Approved
0.5816	Remote Similarity	NPD4250	Approved
0.5812	Remote Similarity	NPD8378	Approved
0.5812	Remote Similarity	NPD8380	Approved
0.5812	Remote Similarity	NPD8379	Approved
0.5812	Remote Similarity	NPD8335	Approved
0.5812	Remote Similarity	NPD8296	Approved
0.5795	Remote Similarity	NPD2254	Approved
0.5795	Remote Similarity	NPD2686	Approved
0.5795	Remote Similarity	NPD2687	Approved
0.5784	Remote Similarity	NPD5282	Discontinued
0.5783	Remote Similarity	NPD368	Approved
0.578	Remote Similarity	NPD6412	Phase 2
0.5773	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD6932	Approved
0.5745	Remote Similarity	NPD7525	Registered
0.5745	Remote Similarity	NPD7509	Discontinued
0.5714	Remote Similarity	NPD7339	Approved
0.5714	Remote Similarity	NPD6942	Approved
0.5699	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD6902	Approved
0.5678	Remote Similarity	NPD7503	Approved
0.5676	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.567	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6053	Discontinued
0.5647	Remote Similarity	NPD371	Approved
0.5638	Remote Similarity	NPD6683	Phase 2
0.563	Remote Similarity	NPD5125	Phase 3
0.563	Remote Similarity	NPD5126	Approved
0.5625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6371	Approved
0.562	Remote Similarity	NPD7507	Approved
0.5618	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6082	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