NPASS Compound

Structure

CID74397 OpenBabel06191715412D 24 25 0 0 1 0 0 0 0 0999 V2000 1.8171 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 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 2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 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 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 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 2.6831 0.3090 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 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 10 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 11 15 1 0 0 0 0 11 20 2 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 19 1 1 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 16 21 1 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.18
Volume:	350.836
LogP:	4.385
LogD:	2.473
LogS:	-3.173
# Rotatable Bonds:	5
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.639
Synthetic Accessibility Score:	3.639
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.709
MDCK Permeability:	1.2236345355631784e-05
Pgp-inhibitor:	0.116
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165
Plasma Protein Binding (PPB):	90.2536849975586%
Volume Distribution (VD):	1.812
Pgp-substrate:	8.053215980529785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.38
CYP1A2-substrate:	0.466
CYP2C19-inhibitor:	0.277
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.366
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.302
CYP3A4-inhibitor:	0.21
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	6.465
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.775
Drug-inuced Liver Injury (DILI):	0.198
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.911
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.63
Carcinogencity:	0.199
Eye Corrosion:	0.003
Eye Irritation:	0.146
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC74397

Natural Product ID:	NPC74397
*Common Name:**	Acronyculatin B
IUPAC Name:	1-[(2R)-4-hydroxy-2-(2-hydroxypropan-2-yl)-6-methoxy-7-(3-methylbut-2-enyl)-2,3-dihydro-1-benzofuran-5-yl]ethanone
Synonyms:	acronyculatin B
Standard InCHIKey:	JWXVSQGKALYNIU-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C19H26O5/c1-10(2)7-8-12-17-13(9-14(24-17)19(4,5)22)16(21)15(11(3)20)18(12)23-6/h7,14,21-22H,8-9H2,1-6H3/t14-/m1/s1
SMILES:	COc1c(CC=C(C)C)c2O[C@H](Cc2c(c1C(=O)C)O)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458308
PubChem CID:	11067612
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000119] Acetophenones

*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]
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
Others	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Inhibition	=	5.3	%	PMID[489255]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	6.5	%	PMID[489255]

☑ 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 NPC74397 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	343
0.1-0.2	1361
0.2-0.3	3784
0.3-0.4	8582
0.4-0.5	10256
0.5-0.6	4186
0.6-0.7	6086
0.7-0.8	5494
0.8-0.85	1817
0.85-0.9	697
0.9-0.95	81
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9568	High Similarity	NPC18886
0.9504	High Similarity	NPC202494
0.9496	High Similarity	NPC276565
0.9441	High Similarity	NPC327059
0.9441	High Similarity	NPC476509
0.9441	High Similarity	NPC470908
0.9441	High Similarity	NPC321387
0.9441	High Similarity	NPC472421
0.9424	High Similarity	NPC171870
0.9375	High Similarity	NPC472423
0.9375	High Similarity	NPC474772
0.9375	High Similarity	NPC471675
0.9375	High Similarity	NPC472636
0.9375	High Similarity	NPC474744
0.9366	High Similarity	NPC470670
0.9366	High Similarity	NPC473133
0.9366	High Similarity	NPC91902
0.9366	High Similarity	NPC47388
0.9362	High Similarity	NPC297788
0.9357	High Similarity	NPC130206
0.931	High Similarity	NPC473996
0.931	High Similarity	NPC31627
0.931	High Similarity	NPC476238
0.931	High Similarity	NPC327269
0.9241	High Similarity	NPC472580
0.9231	High Similarity	NPC85773
0.9231	High Similarity	NPC14875
0.9225	High Similarity	NPC470857
0.922	High Similarity	NPC472344
0.9184	High Similarity	NPC108937
0.9184	High Similarity	NPC279218
0.9178	High Similarity	NPC477957
0.9178	High Similarity	NPC285623
0.9167	High Similarity	NPC10097
0.9161	High Similarity	NPC474302
0.9155	High Similarity	NPC112749
0.9143	High Similarity	NPC37206
0.9143	High Similarity	NPC137009
0.913	High Similarity	NPC101752
0.9122	High Similarity	NPC321372
0.9122	High Similarity	NPC475797
0.9122	High Similarity	NPC474738
0.9122	High Similarity	NPC78554
0.9122	High Similarity	NPC109967
0.9122	High Similarity	NPC469936
0.9122	High Similarity	NPC129053
0.9122	High Similarity	NPC474609
0.911	High Similarity	NPC471677
0.911	High Similarity	NPC472420
0.911	High Similarity	NPC263384
0.911	High Similarity	NPC474021
0.911	High Similarity	NPC244577
0.911	High Similarity	NPC471676
0.911	High Similarity	NPC474023
0.911	High Similarity	NPC472422
0.9103	High Similarity	NPC307052
0.9103	High Similarity	NPC139966
0.9085	High Similarity	NPC112829
0.9085	High Similarity	NPC470556
0.9085	High Similarity	NPC294432
0.9071	High Similarity	NPC131130
0.9065	High Similarity	NPC156910
0.9048	High Similarity	NPC475790
0.9048	High Similarity	NPC256141
0.9041	High Similarity	NPC105136
0.9041	High Similarity	NPC180351
0.9034	High Similarity	NPC168085
0.9028	High Similarity	NPC316769
0.9021	High Similarity	NPC474939
0.9021	High Similarity	NPC307895
0.9021	High Similarity	NPC184738
0.9021	High Similarity	NPC96216
0.9021	High Similarity	NPC470553
0.9021	High Similarity	NPC33653
0.9021	High Similarity	NPC470909
0.9007	High Similarity	NPC23257
0.9007	High Similarity	NPC139554
0.9007	High Similarity	NPC471697
0.9007	High Similarity	NPC270913
0.9	High Similarity	NPC470607
0.8993	High Similarity	NPC84699
0.8986	High Similarity	NPC469405
0.8986	High Similarity	NPC248793
0.8986	High Similarity	NPC180301
0.8986	High Similarity	NPC7989
0.8986	High Similarity	NPC472583
0.8986	High Similarity	NPC223701
0.898	High Similarity	NPC319910
0.898	High Similarity	NPC262039
0.898	High Similarity	NPC262038
0.898	High Similarity	NPC278476
0.898	High Similarity	NPC254412
0.8973	High Similarity	NPC317492
0.8973	High Similarity	NPC472628
0.8966	High Similarity	NPC472627
0.8966	High Similarity	NPC285748
0.8958	High Similarity	NPC288910
0.8958	High Similarity	NPC470890
0.8958	High Similarity	NPC118059
0.8958	High Similarity	NPC224714
0.8958	High Similarity	NPC470554
0.8958	High Similarity	NPC316535
0.8958	High Similarity	NPC133060
0.8944	High Similarity	NPC164697
0.8944	High Similarity	NPC82920
0.8944	High Similarity	NPC289660
0.8944	High Similarity	NPC471587
0.894	High Similarity	NPC328102
0.894	High Similarity	NPC472624
0.894	High Similarity	NPC304839
0.894	High Similarity	NPC220582
0.894	High Similarity	NPC470810
0.8936	High Similarity	NPC470399
0.8936	High Similarity	NPC470672
0.8936	High Similarity	NPC470671
0.8936	High Similarity	NPC474487
0.8936	High Similarity	NPC474504
0.8933	High Similarity	NPC470606
0.8929	High Similarity	NPC187826
0.8929	High Similarity	NPC470397
0.8929	High Similarity	NPC174999
0.8929	High Similarity	NPC470398
0.8926	High Similarity	NPC477958
0.8926	High Similarity	NPC207809
0.8926	High Similarity	NPC48579
0.8926	High Similarity	NPC470681
0.8926	High Similarity	NPC304207
0.8926	High Similarity	NPC259710
0.8926	High Similarity	NPC217706
0.8921	High Similarity	NPC144027
0.8921	High Similarity	NPC236974
0.8919	High Similarity	NPC161881
0.8919	High Similarity	NPC243171
0.8919	High Similarity	NPC35567
0.8919	High Similarity	NPC216035
0.8919	High Similarity	NPC210597
0.8919	High Similarity	NPC217149
0.8919	High Similarity	NPC10807
0.8919	High Similarity	NPC138288
0.8919	High Similarity	NPC150123
0.8919	High Similarity	NPC171651
0.8919	High Similarity	NPC56232
0.8919	High Similarity	NPC244583
0.8913	High Similarity	NPC203817
0.8913	High Similarity	NPC285054
0.8912	High Similarity	NPC38775
0.8912	High Similarity	NPC476185
0.8912	High Similarity	NPC321896
0.8904	High Similarity	NPC472345
0.8897	High Similarity	NPC187282
0.8897	High Similarity	NPC290133
0.8897	High Similarity	NPC24136
0.8897	High Similarity	NPC470910
0.8897	High Similarity	NPC472629
0.8889	High Similarity	NPC316816
0.8889	High Similarity	NPC242100
0.8889	High Similarity	NPC478086
0.8889	High Similarity	NPC255133
0.8889	High Similarity	NPC214166
0.8882	High Similarity	NPC92589
0.8882	High Similarity	NPC74854
0.8882	High Similarity	NPC30655
0.8882	High Similarity	NPC45124
0.8881	High Similarity	NPC248372
0.8881	High Similarity	NPC156190
0.8881	High Similarity	NPC17170
0.8881	High Similarity	NPC166689
0.8881	High Similarity	NPC111201
0.8881	High Similarity	NPC96408
0.8881	High Similarity	NPC279650
0.8881	High Similarity	NPC258630
0.8881	High Similarity	NPC110038
0.8867	High Similarity	NPC17521
0.8867	High Similarity	NPC215917
0.8867	High Similarity	NPC20530
0.8867	High Similarity	NPC10754
0.8859	High Similarity	NPC236756
0.8859	High Similarity	NPC293286
0.8859	High Similarity	NPC100134
0.8859	High Similarity	NPC74924
0.8859	High Similarity	NPC209760
0.8859	High Similarity	NPC311579
0.8857	High Similarity	NPC60667
0.8851	High Similarity	NPC290671
0.8851	High Similarity	NPC209846
0.8851	High Similarity	NPC328740
0.8851	High Similarity	NPC289774
0.8851	High Similarity	NPC477897
0.8849	High Similarity	NPC247743
0.8844	High Similarity	NPC5173
0.8844	High Similarity	NPC89442
0.8836	High Similarity	NPC51070
0.8836	High Similarity	NPC473077
0.8836	High Similarity	NPC296998
0.8836	High Similarity	NPC472918
0.8836	High Similarity	NPC222298
0.8828	High Similarity	NPC131568
0.8828	High Similarity	NPC87486
0.8828	High Similarity	NPC209040
0.8828	High Similarity	NPC131579

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 NPC74397 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	932
0.2-0.3	1986
0.3-0.4	2665
0.4-0.5	1770
0.5-0.6	999
0.6-0.7	359
0.7-0.8	108
0.8-0.85	22
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8873	High Similarity	NPD2800	Approved
0.8733	High Similarity	NPD2393	Clinical (unspecified phase)
0.8699	High Similarity	NPD2533	Approved
0.8699	High Similarity	NPD2532	Approved
0.8699	High Similarity	NPD4378	Clinical (unspecified phase)
0.8699	High Similarity	NPD2534	Approved
0.8658	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD7075	Discontinued
0.8543	High Similarity	NPD1934	Approved
0.8487	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1549	Phase 2
0.8377	Intermediate Similarity	NPD3882	Suspended
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD6651	Approved
0.8312	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD6801	Discontinued
0.8276	Intermediate Similarity	NPD2796	Approved
0.8255	Intermediate Similarity	NPD6799	Approved
0.8247	Intermediate Similarity	NPD2801	Approved
0.8207	Intermediate Similarity	NPD1510	Phase 2
0.8199	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1240	Approved
0.8137	Intermediate Similarity	NPD3818	Discontinued
0.8133	Intermediate Similarity	NPD1511	Approved
0.8125	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6166	Phase 2
0.8117	Intermediate Similarity	NPD7411	Suspended
0.8101	Intermediate Similarity	NPD5494	Approved
0.8069	Intermediate Similarity	NPD1607	Approved
0.8052	Intermediate Similarity	NPD6599	Discontinued
0.805	Intermediate Similarity	NPD6959	Discontinued
0.8049	Intermediate Similarity	NPD6559	Discontinued
0.8026	Intermediate Similarity	NPD1512	Approved
0.8013	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD1243	Approved
0.7974	Intermediate Similarity	NPD920	Approved
0.7962	Intermediate Similarity	NPD3817	Phase 2
0.7927	Intermediate Similarity	NPD7074	Phase 3
0.7919	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5710	Approved
0.7888	Intermediate Similarity	NPD5711	Approved
0.7866	Intermediate Similarity	NPD7054	Approved
0.7843	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7472	Approved
0.7799	Intermediate Similarity	NPD7768	Phase 2
0.7791	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6797	Phase 2
0.775	Intermediate Similarity	NPD3749	Approved
0.7748	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5403	Approved
0.7725	Intermediate Similarity	NPD7251	Discontinued
0.7716	Intermediate Similarity	NPD1247	Approved
0.7702	Intermediate Similarity	NPD919	Approved
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7679	Intermediate Similarity	NPD7808	Phase 3
0.7679	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6232	Discontinued
0.7667	Intermediate Similarity	NPD2935	Discontinued
0.7667	Intermediate Similarity	NPD1551	Phase 2
0.7636	Intermediate Similarity	NPD7473	Discontinued
0.7635	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD5124	Phase 1
0.7632	Intermediate Similarity	NPD2654	Approved
0.7625	Intermediate Similarity	NPD5402	Approved
0.7616	Intermediate Similarity	NPD2344	Approved
0.7613	Intermediate Similarity	NPD5401	Approved
0.7582	Intermediate Similarity	NPD3750	Approved
0.7582	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2424	Discontinued
0.756	Intermediate Similarity	NPD5953	Discontinued
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.7545	Intermediate Similarity	NPD7286	Phase 2
0.7517	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.747	Intermediate Similarity	NPD2403	Approved
0.7456	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6100	Approved
0.7434	Intermediate Similarity	NPD6099	Approved
0.7432	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2313	Discontinued
0.7419	Intermediate Similarity	NPD2309	Approved
0.741	Intermediate Similarity	NPD3926	Phase 2
0.7396	Intermediate Similarity	NPD1729	Discontinued
0.7386	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6005	Phase 3
0.7386	Intermediate Similarity	NPD6002	Phase 3
0.7386	Intermediate Similarity	NPD6004	Phase 3
0.7368	Intermediate Similarity	NPD7033	Discontinued
0.7361	Intermediate Similarity	NPD9717	Approved
0.7355	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD943	Approved
0.7315	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD447	Suspended
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3748	Approved
0.7247	Intermediate Similarity	NPD4360	Phase 2
0.7247	Intermediate Similarity	NPD4363	Phase 3
0.7239	Intermediate Similarity	NPD1465	Phase 2
0.7232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1613	Approved
0.7219	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7390	Discontinued
0.7211	Intermediate Similarity	NPD1203	Approved
0.7207	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4361	Phase 2
0.7205	Intermediate Similarity	NPD3226	Approved
0.72	Intermediate Similarity	NPD8434	Phase 2
0.7189	Intermediate Similarity	NPD7584	Approved
0.7188	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6832	Phase 2
0.7181	Intermediate Similarity	NPD4908	Phase 1
0.7172	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD422	Phase 1
0.7171	Intermediate Similarity	NPD6355	Discontinued
0.7169	Intermediate Similarity	NPD6234	Discontinued
0.7161	Intermediate Similarity	NPD2346	Discontinued
0.7161	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD9545	Approved
0.7133	Intermediate Similarity	NPD3027	Phase 3
0.7117	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD7199	Phase 2
0.7076	Intermediate Similarity	NPD3751	Discontinued
0.7073	Intermediate Similarity	NPD37	Approved
0.707	Intermediate Similarity	NPD1652	Phase 2
0.7067	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1610	Phase 2
0.7048	Intermediate Similarity	NPD4967	Phase 2
0.7048	Intermediate Similarity	NPD4965	Approved
0.7048	Intermediate Similarity	NPD4966	Approved
0.7047	Intermediate Similarity	NPD1019	Discontinued
0.7041	Intermediate Similarity	NPD3787	Discontinued
0.7041	Intermediate Similarity	NPD7229	Phase 3
0.703	Intermediate Similarity	NPD5760	Phase 2
0.703	Intermediate Similarity	NPD5761	Phase 2
0.7029	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD8312	Approved
0.7019	Intermediate Similarity	NPD5049	Phase 3
0.7014	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7458	Discontinued
0.6993	Remote Similarity	NPD9493	Approved
0.6977	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD411	Approved
0.6974	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3268	Approved
0.6966	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4749	Approved
0.6957	Remote Similarity	NPD6782	Approved
0.6957	Remote Similarity	NPD6780	Approved
0.6957	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6777	Approved
0.6957	Remote Similarity	NPD6781	Approved
0.6957	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4661	Approved
0.6957	Remote Similarity	NPD4662	Approved
0.6957	Remote Similarity	NPD6778	Approved
0.6957	Remote Similarity	NPD6779	Approved
0.6957	Remote Similarity	NPD6776	Approved
0.6954	Remote Similarity	NPD3823	Discontinued
0.6949	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD5647	Approved
0.6928	Remote Similarity	NPD6233	Phase 2
0.6928	Remote Similarity	NPD8455	Phase 2
0.6927	Remote Similarity	NPD4287	Approved
0.6927	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4308	Phase 3
0.6914	Remote Similarity	NPD6104	Discontinued
0.6914	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4625	Phase 3
0.6901	Remote Similarity	NPD1241	Discontinued
0.6886	Remote Similarity	NPD2296	Approved
0.6883	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD7228	Approved
0.6875	Remote Similarity	NPD3887	Approved
0.6875	Remote Similarity	NPD2354	Approved
0.6867	Remote Similarity	NPD2797	Approved
0.6863	Remote Similarity	NPD1296	Phase 2
0.6863	Remote Similarity	NPD3764	Approved
0.686	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7435	Discontinued
0.6842	Remote Similarity	NPD8151	Discontinued
0.6839	Remote Similarity	NPD1933	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