NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	570.28
Volume:	597.663
LogP:	6.33
LogD:	2.498
LogS:	-3.689
# Rotatable Bonds:	12
TPSA:	164.75
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.137
Synthetic Accessibility Score:	4.379
Fsp3:	0.438
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.578
MDCK Permeability:	1.031435385812074e-05
Pgp-inhibitor:	0.876
Pgp-substrate:	0.944
Human Intestinal Absorption (HIA):	0.709
20% Bioavailability (F20%):	0.898
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	99.0699462890625%
Volume Distribution (VD):	0.54
Pgp-substrate:	2.063408374786377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.842
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.543
CYP2C9-inhibitor:	0.384
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.373

ADMET: Excretion

Clearance (CL):	2.797
Half-life (T1/2):	0.054

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.934
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.471
Respiratory Toxicity:	0.112

Download Data

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

Natural Product: NPC476508

Natural Product ID:	NPC476508
*Common Name:**	Acrovestenol
IUPAC Name:	1-[3-[1-[3-acetyl-2,6-dihydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-3-methylbutyl]-2,4,6-trihydroxy-5-(2-hydroxy-3-methylbut-3-enyl)phenyl]ethanone
Synonyms:	Acrovestenol
Standard InCHIKey:	SQUFHQRMJAUERE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H42O9/c1-14(2)10-11-19-27(36)25(31(40)24(18(8)34)32(19)41-9)20(12-15(3)4)26-29(38)21(13-22(35)16(5)6)28(37)23(17(7)33)30(26)39/h10,15,20,22,35-40H,5,11-13H2,1-4,6-9H3
SMILES:	COc1c(CC=C(C)C)c(O)c(c(c1C(=O)C)O)C(c1c(O)c(CC(C(=C)C)O)c(c(c1O)C(=O)C)O)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088323
PubChem CID:	70682769
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880321]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[22708987]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22708987]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614422]
NPO40004	Acronychia trifoliolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27797192]
NPO40004	Acronychia trifoliolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27933896]
NPO40004	Acronychia trifoliolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31550158]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12980	Acronychia pedunculata	Species	Rutaceae	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	7

Activity Type	# Activity
Cell Line	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	2700.0	nM	PMID[531393]
NPT1383	Cell Line	A2058	Homo sapiens	IC50	=	2800.0	nM	PMID[531393]
NPT3190	Cell Line	NHDF	Homo sapiens	IC50	>	5000.0	nM	PMID[531393]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[531394]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	10000.0	nM	PMID[531394]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6000.0	nM	PMID[531394]
NPT2	Others	Unspecified		IC50	=	6500.0	nM	PMID[531394]

☑ 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 NPC476508 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	347
0.1-0.2	1289
0.2-0.3	3076
0.3-0.4	7326
0.4-0.5	11748
0.5-0.6	4313
0.6-0.7	6154
0.7-0.8	5965
0.8-0.85	1606
0.85-0.9	806
0.9-0.95	61
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9704	High Similarity	NPC322301
0.9704	High Similarity	NPC255801
0.9407	High Similarity	NPC16197
0.9333	High Similarity	NPC15834
0.9333	High Similarity	NPC215875
0.9306	High Similarity	NPC476509
0.9286	High Similarity	NPC321980
0.9286	High Similarity	NPC470087
0.9185	High Similarity	NPC279566
0.9178	High Similarity	NPC43345
0.9161	High Similarity	NPC470910
0.9155	High Similarity	NPC245482
0.9155	High Similarity	NPC51887
0.9155	High Similarity	NPC476178
0.9155	High Similarity	NPC475705
0.9155	High Similarity	NPC117836
0.9155	High Similarity	NPC301751
0.9149	High Similarity	NPC470089
0.9143	High Similarity	NPC470211
0.913	High Similarity	NPC84699
0.9122	High Similarity	NPC474386
0.9111	High Similarity	NPC186628
0.911	High Similarity	NPC476551
0.911	High Similarity	NPC476553
0.911	High Similarity	NPC476552
0.9091	High Similarity	NPC470890
0.9091	High Similarity	NPC118059
0.9091	High Similarity	NPC288910
0.9091	High Similarity	NPC133060
0.9091	High Similarity	NPC470554
0.9091	High Similarity	NPC328623
0.9091	High Similarity	NPC224714
0.9085	High Similarity	NPC297600
0.9085	High Similarity	NPC148545
0.9058	High Similarity	NPC103842
0.9051	High Similarity	NPC285054
0.9034	High Similarity	NPC145467
0.9028	High Similarity	NPC472629
0.9028	High Similarity	NPC316769
0.9021	High Similarity	NPC18886
0.9021	High Similarity	NPC474939
0.9021	High Similarity	NPC96216
0.9021	High Similarity	NPC307895
0.9021	High Similarity	NPC184738
0.9021	High Similarity	NPC470553
0.9021	High Similarity	NPC33653
0.9021	High Similarity	NPC470909
0.9014	High Similarity	NPC469404
0.9007	High Similarity	NPC283429
0.9007	High Similarity	NPC477956
0.9	High Similarity	NPC153979
0.8993	High Similarity	NPC156092
0.8993	High Similarity	NPC13575
0.898	High Similarity	NPC178484
0.8973	High Similarity	NPC89442
0.8966	High Similarity	NPC261271
0.8966	High Similarity	NPC308200
0.8966	High Similarity	NPC222298
0.8966	High Similarity	NPC475348
0.8966	High Similarity	NPC51070
0.8958	High Similarity	NPC124780
0.8958	High Similarity	NPC235217
0.8958	High Similarity	NPC473014
0.8958	High Similarity	NPC87486
0.8958	High Similarity	NPC271288
0.8951	High Similarity	NPC276565
0.8951	High Similarity	NPC112829
0.8951	High Similarity	NPC294432
0.8951	High Similarity	NPC470556
0.8944	High Similarity	NPC259166
0.8944	High Similarity	NPC144118
0.8944	High Similarity	NPC80962
0.8944	High Similarity	NPC326109
0.8944	High Similarity	NPC219917
0.8944	High Similarity	NPC11056
0.8944	High Similarity	NPC204985
0.8944	High Similarity	NPC253822
0.8944	High Similarity	NPC172250
0.8944	High Similarity	NPC215311
0.8944	High Similarity	NPC265178
0.8944	High Similarity	NPC213659
0.8944	High Similarity	NPC48624
0.8936	High Similarity	NPC471620
0.8936	High Similarity	NPC21350
0.8933	High Similarity	NPC257166
0.8933	High Similarity	NPC208258
0.8929	High Similarity	NPC477242
0.8929	High Similarity	NPC41461
0.8929	High Similarity	NPC477244
0.8929	High Similarity	NPC477243
0.8929	High Similarity	NPC213603
0.8929	High Similarity	NPC25287
0.8929	High Similarity	NPC249606
0.8929	High Similarity	NPC1486
0.8929	High Similarity	NPC12165
0.8929	High Similarity	NPC98115
0.8929	High Similarity	NPC66349
0.8929	High Similarity	NPC186838
0.8929	High Similarity	NPC24394
0.8929	High Similarity	NPC150399
0.8929	High Similarity	NPC168105
0.8929	High Similarity	NPC274109
0.8926	High Similarity	NPC37253
0.8926	High Similarity	NPC79375
0.8912	High Similarity	NPC474735
0.8904	High Similarity	NPC470460
0.8904	High Similarity	NPC152233
0.8904	High Similarity	NPC39195
0.8897	High Similarity	NPC285630
0.8897	High Similarity	NPC187282
0.8897	High Similarity	NPC290133
0.8897	High Similarity	NPC24136
0.8897	High Similarity	NPC127059
0.8889	High Similarity	NPC185276
0.8889	High Similarity	NPC77794
0.8889	High Similarity	NPC85162
0.8889	High Similarity	NPC125894
0.8889	High Similarity	NPC223812
0.8889	High Similarity	NPC278249
0.8889	High Similarity	NPC107177
0.8889	High Similarity	NPC81697
0.8889	High Similarity	NPC112749
0.8882	High Similarity	NPC472346
0.8881	High Similarity	NPC248372
0.8881	High Similarity	NPC26051
0.8881	High Similarity	NPC40118
0.8881	High Similarity	NPC157497
0.8881	High Similarity	NPC285659
0.8881	High Similarity	NPC52789
0.8881	High Similarity	NPC156190
0.8881	High Similarity	NPC232021
0.8881	High Similarity	NPC81337
0.8881	High Similarity	NPC17170
0.8881	High Similarity	NPC166689
0.8881	High Similarity	NPC96408
0.8881	High Similarity	NPC279650
0.8881	High Similarity	NPC268204
0.8881	High Similarity	NPC126534
0.8881	High Similarity	NPC258630
0.8881	High Similarity	NPC55832
0.8881	High Similarity	NPC110038
0.8874	High Similarity	NPC51247
0.8874	High Similarity	NPC15815
0.8873	High Similarity	NPC472366
0.8873	High Similarity	NPC139554
0.8873	High Similarity	NPC240305
0.8873	High Similarity	NPC295384
0.8867	High Similarity	NPC10754
0.8867	High Similarity	NPC20530
0.8867	High Similarity	NPC215917
0.8865	High Similarity	NPC472419
0.8865	High Similarity	NPC317119
0.8859	High Similarity	NPC324447
0.8857	High Similarity	NPC131039
0.8851	High Similarity	NPC471677
0.8849	High Similarity	NPC28753
0.8849	High Similarity	NPC18877
0.8849	High Similarity	NPC204960
0.8849	High Similarity	NPC159623
0.8849	High Similarity	NPC20560
0.8849	High Similarity	NPC294593
0.8849	High Similarity	NPC144051
0.8849	High Similarity	NPC82225
0.8844	High Similarity	NPC139966
0.8844	High Similarity	NPC470461
0.8844	High Similarity	NPC307052
0.8844	High Similarity	NPC5173
0.8844	High Similarity	NPC473016
0.8844	High Similarity	NPC471114
0.8841	High Similarity	NPC27490
0.8836	High Similarity	NPC473133
0.8836	High Similarity	NPC300988
0.8836	High Similarity	NPC47388
0.8836	High Similarity	NPC470670
0.8836	High Similarity	NPC91902
0.8836	High Similarity	NPC10990
0.8828	High Similarity	NPC473015
0.8828	High Similarity	NPC311144
0.8828	High Similarity	NPC131568
0.8828	High Similarity	NPC194949
0.8828	High Similarity	NPC282957
0.8828	High Similarity	NPC131579
0.8828	High Similarity	NPC476055
0.8828	High Similarity	NPC236766
0.8828	High Similarity	NPC473013
0.8828	High Similarity	NPC197252
0.8819	High Similarity	NPC228504
0.8819	High Similarity	NPC324436
0.8819	High Similarity	NPC328164
0.8819	High Similarity	NPC223500
0.8819	High Similarity	NPC177354
0.8819	High Similarity	NPC167624
0.8819	High Similarity	NPC107572
0.8819	High Similarity	NPC220998
0.8819	High Similarity	NPC166934
0.8819	High Similarity	NPC227579
0.8819	High Similarity	NPC265040
0.8819	High Similarity	NPC1089
0.8819	High Similarity	NPC472344
0.8819	High Similarity	NPC296917

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 NPC476508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	924
0.2-0.3	1707
0.3-0.4	2613
0.4-0.5	1987
0.5-0.6	1097
0.6-0.7	360
0.7-0.8	126
0.8-0.85	23
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8926	High Similarity	NPD8443	Clinical (unspecified phase)
0.8849	High Similarity	NPD6651	Approved
0.8784	High Similarity	NPD4380	Phase 2
0.8699	High Similarity	NPD4378	Clinical (unspecified phase)
0.8592	High Similarity	NPD1510	Phase 2
0.8571	High Similarity	NPD1240	Approved
0.8487	Intermediate Similarity	NPD7819	Suspended
0.8487	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD2800	Approved
0.8472	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1607	Approved
0.8446	Intermediate Similarity	NPD2532	Approved
0.8446	Intermediate Similarity	NPD2534	Approved
0.8446	Intermediate Similarity	NPD2533	Approved
0.8446	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD7075	Discontinued
0.8414	Intermediate Similarity	NPD1549	Phase 2
0.8313	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6959	Discontinued
0.8276	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7411	Suspended
0.8205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD1934	Approved
0.8182	Intermediate Similarity	NPD6801	Discontinued
0.8163	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD7768	Phase 2
0.8125	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2935	Discontinued
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7927	Intermediate Similarity	NPD7074	Phase 3
0.7898	Intermediate Similarity	NPD2801	Approved
0.7895	Intermediate Similarity	NPD6799	Approved
0.7895	Intermediate Similarity	NPD1511	Approved
0.7875	Intermediate Similarity	NPD5494	Approved
0.7866	Intermediate Similarity	NPD7054	Approved
0.7821	Intermediate Similarity	NPD6599	Discontinued
0.7818	Intermediate Similarity	NPD7472	Approved
0.7815	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3818	Discontinued
0.7799	Intermediate Similarity	NPD3882	Suspended
0.7793	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1512	Approved
0.7784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD5710	Approved
0.7778	Intermediate Similarity	NPD5711	Approved
0.7778	Intermediate Similarity	NPD7390	Discontinued
0.7748	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD3817	Phase 2
0.7725	Intermediate Similarity	NPD7251	Discontinued
0.7725	Intermediate Similarity	NPD6559	Discontinued
0.7718	Intermediate Similarity	NPD2799	Discontinued
0.7718	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3750	Approved
0.7688	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1551	Phase 2
0.7665	Intermediate Similarity	NPD5953	Discontinued
0.7665	Intermediate Similarity	NPD6797	Phase 2
0.7651	Intermediate Similarity	NPD7286	Phase 2
0.7632	Intermediate Similarity	NPD1243	Approved
0.7628	Intermediate Similarity	NPD5403	Approved
0.7628	Intermediate Similarity	NPD920	Approved
0.7582	Intermediate Similarity	NPD4628	Phase 3
0.7551	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6099	Approved
0.755	Intermediate Similarity	NPD6100	Approved
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.7543	Intermediate Similarity	NPD4360	Phase 2
0.7543	Intermediate Similarity	NPD4363	Phase 3
0.7531	Intermediate Similarity	NPD3749	Approved
0.7529	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5124	Phase 1
0.7517	Intermediate Similarity	NPD2798	Approved
0.7516	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD943	Approved
0.7432	Intermediate Similarity	NPD2313	Discontinued
0.7421	Intermediate Similarity	NPD7458	Discontinued
0.7421	Intermediate Similarity	NPD3226	Approved
0.7415	Intermediate Similarity	NPD6832	Phase 2
0.7415	Intermediate Similarity	NPD4908	Phase 1
0.7403	Intermediate Similarity	NPD2654	Approved
0.7391	Intermediate Similarity	NPD37	Approved
0.7368	Intermediate Similarity	NPD3748	Approved
0.736	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8312	Approved
0.7326	Intermediate Similarity	NPD8313	Approved
0.7308	Intermediate Similarity	NPD2309	Approved
0.7303	Intermediate Similarity	NPD4361	Phase 2
0.7303	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1610	Phase 2
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7256	Intermediate Similarity	NPD4966	Approved
0.7256	Intermediate Similarity	NPD4967	Phase 2
0.7256	Intermediate Similarity	NPD4965	Approved
0.7255	Intermediate Similarity	NPD7033	Discontinued
0.7248	Intermediate Similarity	NPD3027	Phase 3
0.7241	Intermediate Similarity	NPD3972	Approved
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1203	Approved
0.7204	Intermediate Similarity	NPD8151	Discontinued
0.7202	Intermediate Similarity	NPD3926	Phase 2
0.72	Intermediate Similarity	NPD3268	Approved
0.72	Intermediate Similarity	NPD8150	Discontinued
0.72	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1247	Approved
0.7172	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD230	Phase 1
0.717	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6234	Discontinued
0.7169	Intermediate Similarity	NPD919	Approved
0.7162	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6004	Phase 3
0.7161	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6002	Phase 3
0.7161	Intermediate Similarity	NPD6005	Phase 3
0.7161	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7134	Intermediate Similarity	NPD1465	Phase 2
0.7134	Intermediate Similarity	NPD8455	Phase 2
0.7134	Intermediate Similarity	NPD7003	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.7099	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7584	Approved
0.7097	Intermediate Similarity	NPD5405	Approved
0.7097	Intermediate Similarity	NPD5408	Approved
0.7097	Intermediate Similarity	NPD5406	Approved
0.7097	Intermediate Similarity	NPD5404	Approved
0.7095	Intermediate Similarity	NPD1164	Approved
0.7095	Intermediate Similarity	NPD2797	Approved
0.7086	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7871	Phase 2
0.7081	Intermediate Similarity	NPD7870	Phase 2
0.7076	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7228	Approved
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7055	Intermediate Similarity	NPD1201	Approved
0.7049	Intermediate Similarity	NPD6777	Approved
0.7049	Intermediate Similarity	NPD6780	Approved
0.7049	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6778	Approved
0.7049	Intermediate Similarity	NPD6781	Approved
0.7049	Intermediate Similarity	NPD6782	Approved
0.7049	Intermediate Similarity	NPD6779	Approved
0.7049	Intermediate Similarity	NPD6776	Approved
0.7045	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5760	Phase 2
0.703	Intermediate Similarity	NPD5761	Phase 2
0.7027	Intermediate Similarity	NPD7435	Discontinued
0.7027	Intermediate Similarity	NPD1876	Approved
0.7014	Intermediate Similarity	NPD1548	Phase 1
0.7014	Intermediate Similarity	NPD9545	Approved
0.7007	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD9717	Approved
0.6994	Remote Similarity	NPD1729	Discontinued
0.6993	Remote Similarity	NPD9493	Approved
0.6993	Remote Similarity	NPD1613	Approved
0.6993	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7199	Phase 2
0.698	Remote Similarity	NPD1470	Approved
0.6974	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7701	Phase 2
0.6959	Remote Similarity	NPD2403	Approved
0.6948	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7801	Approved
0.694	Remote Similarity	NPD7699	Phase 2
0.694	Remote Similarity	NPD7700	Phase 2
0.6939	Remote Similarity	NPD422	Phase 1
0.6914	Remote Similarity	NPD7685	Pre-registration
0.6913	Remote Similarity	NPD1283	Approved
0.6908	Remote Similarity	NPD4625	Phase 3
0.6899	Remote Similarity	NPD2424	Discontinued
0.6895	Remote Similarity	NPD7874	Approved
0.6895	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2861	Phase 2
0.6882	Remote Similarity	NPD6823	Phase 2
0.6879	Remote Similarity	NPD3751	Discontinued
0.6868	Remote Similarity	NPD6534	Approved
0.6868	Remote Similarity	NPD6535	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