NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	672.28
Volume:	667.598
LogP:	2.901
LogD:	1.855
LogS:	-4.463
# Rotatable Bonds:	15
TPSA:	181.19
# H-Bond Aceptor:	13
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.211
Synthetic Accessibility Score:	6.326
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.238
MDCK Permeability:	6.441232835641131e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.813
Human Intestinal Absorption (HIA):	0.471
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	55.81069564819336%
Volume Distribution (VD):	0.954
Pgp-substrate:	19.234634399414062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.453
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.181
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.548

ADMET: Excretion

Clearance (CL):	5.508
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.096
Skin Sensitization:	0.735
Carcinogencity:	0.285
Eye Corrosion:	0.016
Eye Irritation:	0.031
Respiratory Toxicity:	0.637

Download Data

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

Natural Product: NPC476976

Natural Product ID:	NPC476976
*Common Name:**	[(1S,2S,5S,6S,7R,8S,9R,12R)-12-acetyloxy-5-(2-acetyloxyacetyl)oxy-2,8-dihydroxy-2,6,10-trimethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-10-yl]methyl (E)-2-methylbut-2-enoate
IUPAC Name:	[(1S,2S,5S,6S,7R,8S,9R,12R)-12-acetyloxy-5-(2-acetyloxyacetyl)oxy-2,8-dihydroxy-2,6,10-trimethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-10-yl]methyl (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	YHCKEIOMLBIUQU-SEHFLPBWSA-N
Standard InCHI:	InChI=1S/C35H44O13/c1-8-20(2)31(41)44-19-32(5)27-28(40)30(47-25(38)15-14-23-12-10-9-11-13-23)34(7)24(46-26(39)18-43-21(3)36)16-17-33(6,42)35(34,48-32)29(27)45-22(4)37/h8-15,24,27-30,40,42H,16-19H2,1-7H3/b15-14+,20-8+/t24-,27+,28-,29+,30-,32?,33-,34-,35-/m0/s1
SMILES:	C/C=C(\C)/C(=O)OCC1([C@@H]2[C@@H]([C@@H]([C@@]3([C@H](CC[C@]([C@]3([C@@H]2OC(=O)C)O1)(C)O)OC(=O)COC(=O)C)C)OC(=O)/C=C/C4=CC=CC=C4)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118726322
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO33650	Denhamia celastroides	Species	Celastraceae	Eukaryota	leave	Walton Bridge Reserve, The Gap, Australia	2012-OCT	PMID[25579619]

☑ 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
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	10000	nM	PMID[25579619]

☑ 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 NPC476976 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	239
0.1-0.2	961
0.2-0.3	2162
0.3-0.4	4866
0.4-0.5	8605
0.5-0.6	17446
0.6-0.7	7299
0.7-0.8	842
0.8-0.85	140
0.85-0.9	108
0.9-0.95	12
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC476977
0.9597	High Similarity	NPC476971
0.9597	High Similarity	NPC476972
0.9516	High Similarity	NPC470158
0.9516	High Similarity	NPC476970
0.9516	High Similarity	NPC475933
0.928	High Similarity	NPC473083
0.9274	High Similarity	NPC473871
0.9274	High Similarity	NPC473870
0.9194	High Similarity	NPC70973
0.9194	High Similarity	NPC473889
0.9113	High Similarity	NPC311175
0.9113	High Similarity	NPC37641
0.9055	High Similarity	NPC473111
0.9055	High Similarity	NPC473110
0.9055	High Similarity	NPC473082
0.8978	High Similarity	NPC301946
0.8978	High Similarity	NPC277053
0.8976	High Similarity	NPC114927
0.8921	High Similarity	NPC476975
0.8905	High Similarity	NPC471912
0.8905	High Similarity	NPC80895
0.8871	High Similarity	NPC473860
0.8857	High Similarity	NPC470245
0.8857	High Similarity	NPC473214
0.8828	High Similarity	NPC471758
0.8824	High Similarity	NPC41481
0.8824	High Similarity	NPC291599
0.8824	High Similarity	NPC97947
0.8824	High Similarity	NPC16912
0.8824	High Similarity	NPC118080
0.8824	High Similarity	NPC472576
0.8824	High Similarity	NPC87448
0.8824	High Similarity	NPC27377
0.879	High Similarity	NPC84129
0.8786	High Similarity	NPC473215
0.876	High Similarity	NPC45821
0.875	High Similarity	NPC171207
0.875	High Similarity	NPC90614
0.875	High Similarity	NPC275592
0.875	High Similarity	NPC100913
0.875	High Similarity	NPC97667
0.8705	High Similarity	NPC174982
0.8705	High Similarity	NPC472571
0.8705	High Similarity	NPC177940
0.8705	High Similarity	NPC472572
0.8705	High Similarity	NPC200471
0.8705	High Similarity	NPC476973
0.8705	High Similarity	NPC472568
0.8705	High Similarity	NPC29704
0.8705	High Similarity	NPC473088
0.8705	High Similarity	NPC470157
0.8705	High Similarity	NPC472575
0.8705	High Similarity	NPC184817
0.8705	High Similarity	NPC469349
0.8705	High Similarity	NPC96903
0.8705	High Similarity	NPC471104
0.8705	High Similarity	NPC158663
0.8705	High Similarity	NPC470159
0.8705	High Similarity	NPC70403
0.8705	High Similarity	NPC171525
0.8702	High Similarity	NPC93632
0.8672	High Similarity	NPC12016
0.8662	High Similarity	NPC471103
0.8662	High Similarity	NPC470153
0.8662	High Similarity	NPC51602
0.8633	High Similarity	NPC241951
0.8633	High Similarity	NPC125106
0.8633	High Similarity	NPC25768
0.8633	High Similarity	NPC95810
0.8633	High Similarity	NPC57628
0.8633	High Similarity	NPC476974
0.8633	High Similarity	NPC472569
0.8633	High Similarity	NPC470152
0.8633	High Similarity	NPC472573
0.8633	High Similarity	NPC472570
0.8633	High Similarity	NPC475122
0.8633	High Similarity	NPC188865
0.8633	High Similarity	NPC475759
0.8633	High Similarity	NPC95265
0.8633	High Similarity	NPC163719
0.8633	High Similarity	NPC11685
0.8633	High Similarity	NPC70716
0.8626	High Similarity	NPC58061
0.8623	High Similarity	NPC472546
0.8605	High Similarity	NPC472373
0.8561	High Similarity	NPC163087
0.8552	High Similarity	NPC106895
0.8548	High Similarity	NPC473869
0.8538	High Similarity	NPC284022
0.8521	High Similarity	NPC270590
0.8521	High Similarity	NPC92293
0.8521	High Similarity	NPC301556
0.8521	High Similarity	NPC266265
0.8521	High Similarity	NPC471101
0.8516	High Similarity	NPC300827
0.8516	High Similarity	NPC473439
0.8511	High Similarity	NPC474935
0.8507	High Similarity	NPC80599
0.85	High Similarity	NPC470231
0.8489	Intermediate Similarity	NPC34012
0.8489	Intermediate Similarity	NPC473755
0.8489	Intermediate Similarity	NPC475513
0.8485	Intermediate Similarity	NPC230331
0.8483	Intermediate Similarity	NPC21410
0.8483	Intermediate Similarity	NPC282239
0.8483	Intermediate Similarity	NPC473670
0.8478	Intermediate Similarity	NPC472547
0.8456	Intermediate Similarity	NPC195647
0.8456	Intermediate Similarity	NPC472577
0.8456	Intermediate Similarity	NPC66761
0.8456	Intermediate Similarity	NPC17877
0.8456	Intermediate Similarity	NPC291638
0.8451	Intermediate Similarity	NPC281717
0.845	Intermediate Similarity	NPC475328
0.844	Intermediate Similarity	NPC472556
0.8382	Intermediate Similarity	NPC474608
0.8367	Intermediate Similarity	NPC477470
0.8367	Intermediate Similarity	NPC477474
0.8367	Intermediate Similarity	NPC472393
0.8367	Intermediate Similarity	NPC477472
0.8358	Intermediate Similarity	NPC473443
0.8357	Intermediate Similarity	NPC182869
0.8356	Intermediate Similarity	NPC472549
0.8345	Intermediate Similarity	NPC211137
0.8345	Intermediate Similarity	NPC48017
0.8345	Intermediate Similarity	NPC473613
0.8345	Intermediate Similarity	NPC473060
0.8345	Intermediate Similarity	NPC4341
0.8345	Intermediate Similarity	NPC476094
0.8345	Intermediate Similarity	NPC200592
0.8345	Intermediate Similarity	NPC473112
0.8345	Intermediate Similarity	NPC147880
0.8345	Intermediate Similarity	NPC473085
0.8345	Intermediate Similarity	NPC184747
0.8345	Intermediate Similarity	NPC473109
0.8345	Intermediate Similarity	NPC43241
0.8345	Intermediate Similarity	NPC473081
0.8345	Intermediate Similarity	NPC473758
0.8333	Intermediate Similarity	NPC39549
0.8333	Intermediate Similarity	NPC7095
0.8311	Intermediate Similarity	NPC471102
0.8311	Intermediate Similarity	NPC477467
0.831	Intermediate Similarity	NPC471100
0.831	Intermediate Similarity	NPC471107
0.831	Intermediate Similarity	NPC127857
0.8308	Intermediate Similarity	NPC473749
0.8299	Intermediate Similarity	NPC217091
0.8288	Intermediate Similarity	NPC69425
0.8286	Intermediate Similarity	NPC224491
0.8284	Intermediate Similarity	NPC225103
0.8281	Intermediate Similarity	NPC89324
0.8273	Intermediate Similarity	NPC475652
0.8273	Intermediate Similarity	NPC214550
0.8273	Intermediate Similarity	NPC210591
0.8271	Intermediate Similarity	NPC171007
0.8271	Intermediate Similarity	NPC190849
0.8268	Intermediate Similarity	NPC470820
0.8264	Intermediate Similarity	NPC60509
0.8264	Intermediate Similarity	NPC81698
0.8264	Intermediate Similarity	NPC250046
0.8264	Intermediate Similarity	NPC474564
0.8261	Intermediate Similarity	NPC472545
0.8261	Intermediate Similarity	NPC472551
0.8252	Intermediate Similarity	NPC473602
0.8252	Intermediate Similarity	NPC240115
0.8239	Intermediate Similarity	NPC38696
0.8239	Intermediate Similarity	NPC34943
0.8239	Intermediate Similarity	NPC471139
0.8235	Intermediate Similarity	NPC209851
0.8231	Intermediate Similarity	NPC132599
0.8231	Intermediate Similarity	NPC469730
0.8231	Intermediate Similarity	NPC228204
0.8231	Intermediate Similarity	NPC26033
0.8231	Intermediate Similarity	NPC473632
0.8231	Intermediate Similarity	NPC473611
0.8227	Intermediate Similarity	NPC140021
0.8222	Intermediate Similarity	NPC475138
0.8222	Intermediate Similarity	NPC472388
0.8219	Intermediate Similarity	NPC477905
0.8219	Intermediate Similarity	NPC472548
0.8209	Intermediate Similarity	NPC195224
0.8207	Intermediate Similarity	NPC254558
0.8207	Intermediate Similarity	NPC476092
0.8207	Intermediate Similarity	NPC475447
0.8207	Intermediate Similarity	NPC112216
0.8207	Intermediate Similarity	NPC475218
0.8207	Intermediate Similarity	NPC161239
0.8207	Intermediate Similarity	NPC70236
0.8207	Intermediate Similarity	NPC165260
0.8207	Intermediate Similarity	NPC198455
0.8201	Intermediate Similarity	NPC283375
0.8201	Intermediate Similarity	NPC183122
0.8201	Intermediate Similarity	NPC184109
0.8194	Intermediate Similarity	NPC473760
0.8182	Intermediate Similarity	NPC470815
0.8175	Intermediate Similarity	NPC15850
0.8169	Intermediate Similarity	NPC91703
0.8169	Intermediate Similarity	NPC477894
0.8169	Intermediate Similarity	NPC473673

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 NPC476976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	654
0.2-0.3	1464
0.3-0.4	3235
0.4-0.5	2217
0.5-0.6	1117
0.6-0.7	239
0.7-0.8	18
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
0.7914	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD4198	Discontinued
0.7568	Intermediate Similarity	NPD7236	Approved
0.75	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7741	Discontinued
0.7455	Intermediate Similarity	NPD8407	Phase 2
0.7453	Intermediate Similarity	NPD7799	Discontinued
0.7434	Intermediate Similarity	NPD7239	Suspended
0.7407	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD8368	Discontinued
0.7343	Intermediate Similarity	NPD7961	Discontinued
0.7267	Intermediate Similarity	NPD6190	Approved
0.7262	Intermediate Similarity	NPD8434	Phase 2
0.7226	Intermediate Similarity	NPD5126	Approved
0.7226	Intermediate Similarity	NPD5125	Phase 3
0.7176	Intermediate Similarity	NPD8435	Approved
0.7164	Intermediate Similarity	NPD2629	Approved
0.7101	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD8361	Approved
0.7076	Intermediate Similarity	NPD8360	Approved
0.7059	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD7057	Phase 3
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD7058	Phase 2
0.7	Intermediate Similarity	NPD5763	Approved
0.6977	Remote Similarity	NPD6647	Phase 2
0.6974	Remote Similarity	NPD8166	Discontinued
0.6947	Remote Similarity	NPD6685	Approved
0.6932	Remote Similarity	NPD8485	Approved
0.6889	Remote Similarity	NPD6858	Approved
0.6889	Remote Similarity	NPD7094	Approved
0.6887	Remote Similarity	NPD7266	Discontinued
0.6884	Remote Similarity	NPD7516	Approved
0.6849	Remote Similarity	NPD7095	Approved
0.6816	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD37	Approved
0.6812	Remote Similarity	NPD7327	Approved
0.6812	Remote Similarity	NPD7328	Approved
0.6791	Remote Similarity	NPD2067	Discontinued
0.679	Remote Similarity	NPD4966	Approved
0.679	Remote Similarity	NPD4965	Approved
0.679	Remote Similarity	NPD4967	Phase 2
0.6763	Remote Similarity	NPD8150	Discontinued
0.6759	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5765	Approved
0.6716	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6010	Discontinued
0.6712	Remote Similarity	NPD5736	Approved
0.6707	Remote Similarity	NPD6234	Discontinued
0.6705	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5344	Discontinued
0.6691	Remote Similarity	NPD6912	Phase 3
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6646	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4628	Phase 3
0.6627	Remote Similarity	NPD7228	Approved
0.6618	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5048	Discontinued
0.6615	Remote Similarity	NPD6648	Approved
0.6615	Remote Similarity	NPD7640	Approved
0.6615	Remote Similarity	NPD7639	Approved
0.6615	Remote Similarity	NPD7798	Approved
0.66	Remote Similarity	NPD4060	Phase 1
0.66	Remote Similarity	NPD4140	Approved
0.6596	Remote Similarity	NPD8377	Approved
0.6596	Remote Similarity	NPD8294	Approved
0.6575	Remote Similarity	NPD3094	Phase 2
0.6573	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8297	Approved
0.6569	Remote Similarity	NPD969	Suspended
0.6564	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8033	Approved
0.6548	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7075	Discontinued
0.6544	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5909	Discontinued
0.6538	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4225	Approved
0.6533	Remote Similarity	NPD6663	Approved
0.6533	Remote Similarity	NPD6233	Phase 2
0.6525	Remote Similarity	NPD7610	Discontinued
0.6519	Remote Similarity	NPD6686	Approved
0.6519	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7008	Discontinued
0.6508	Remote Similarity	NPD8462	Phase 1
0.6491	Remote Similarity	NPD5844	Phase 1
0.6481	Remote Similarity	NPD6599	Discontinued
0.6479	Remote Similarity	NPD6319	Approved
0.6475	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6765	Approved
0.6474	Remote Similarity	NPD7240	Approved
0.6474	Remote Similarity	NPD6764	Approved
0.6471	Remote Similarity	NPD7097	Phase 1
0.6467	Remote Similarity	NPD6798	Discontinued
0.6467	Remote Similarity	NPD3764	Approved
0.6466	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5735	Approved
0.6438	Remote Similarity	NPD6273	Approved
0.6429	Remote Similarity	NPD5951	Approved
0.6429	Remote Similarity	NPD7199	Phase 2
0.6424	Remote Similarity	NPD5402	Approved
0.6414	Remote Similarity	NPD3092	Approved
0.6402	Remote Similarity	NPD6801	Discontinued
0.6395	Remote Similarity	NPD7736	Approved
0.6378	Remote Similarity	NPD7838	Discovery
0.6377	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.637	Remote Similarity	NPD7507	Approved
0.637	Remote Similarity	NPD6637	Approved
0.6369	Remote Similarity	NPD6674	Discontinued
0.6364	Remote Similarity	NPD8455	Phase 2
0.6364	Remote Similarity	NPD7819	Suspended
0.6351	Remote Similarity	NPD7319	Approved
0.634	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5124	Phase 1
0.6337	Remote Similarity	NPD3751	Discontinued
0.6328	Remote Similarity	NPD6785	Approved
0.6328	Remote Similarity	NPD6784	Approved
0.6325	Remote Similarity	NPD3817	Phase 2
0.6324	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.631	Remote Similarity	NPD8319	Approved
0.631	Remote Similarity	NPD8320	Phase 1
0.6308	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6049	Phase 2
0.6307	Remote Similarity	NPD8312	Approved
0.6307	Remote Similarity	NPD8313	Approved
0.6301	Remote Similarity	NPD7492	Approved
0.6301	Remote Similarity	NPD4806	Approved
0.6301	Remote Similarity	NPD4807	Approved
0.6296	Remote Similarity	NPD5403	Approved
0.6294	Remote Similarity	NPD3787	Discontinued
0.6289	Remote Similarity	NPD8404	Phase 2
0.6288	Remote Similarity	NPD5926	Approved
0.6287	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4632	Approved
0.6284	Remote Similarity	NPD8651	Approved
0.6279	Remote Similarity	NPD7473	Discontinued
0.6277	Remote Similarity	NPD6899	Approved
0.6277	Remote Similarity	NPD6881	Approved
0.6276	Remote Similarity	NPD3095	Discontinued
0.6276	Remote Similarity	NPD5305	Approved
0.6276	Remote Similarity	NPD5306	Approved
0.6275	Remote Similarity	NPD3620	Phase 2
0.6275	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5401	Approved
0.6268	Remote Similarity	NPD7115	Discovery
0.6265	Remote Similarity	NPD5761	Phase 2
0.6265	Remote Similarity	NPD5760	Phase 2
0.6259	Remote Similarity	NPD6649	Approved
0.6259	Remote Similarity	NPD6616	Approved
0.6259	Remote Similarity	NPD8130	Phase 1
0.6259	Remote Similarity	NPD6650	Approved
0.6258	Remote Similarity	NPD5886	Approved
0.6258	Remote Similarity	NPD1653	Approved
0.6258	Remote Similarity	NPD41	Approved
0.6257	Remote Similarity	NPD7435	Discontinued
0.6257	Remote Similarity	NPD7497	Discontinued
0.625	Remote Similarity	NPD7699	Phase 2
0.625	Remote Similarity	NPD3091	Approved
0.625	Remote Similarity	NPD7700	Phase 2
0.625	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD7985	Registered
0.6242	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD6002	Phase 3
0.6242	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD6005	Phase 3
0.6242	Remote Similarity	NPD6004	Phase 3
0.6241	Remote Similarity	NPD2066	Phase 3
0.6233	Remote Similarity	NPD8328	Phase 3
0.6232	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4110	Phase 3
0.6226	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD2575	Approved
0.6224	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7458	Discontinued
0.622	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7305	Phase 1
0.6216	Remote Similarity	NPD7078	Approved
0.6214	Remote Similarity	NPD6882	Approved
0.6213	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6799	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