NPASS Compound

Structure

CID223451 OpenBabel06191716022D 24 25 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 16 2 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 14 17 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 6 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	156.15
Volume:	181.75
LogP:	3.022
LogD:	3.25
LogS:	-2.73
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	3.353
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.323
MDCK Permeability:	2.731731910898816e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.375

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.832
Plasma Protein Binding (PPB):	82.25637817382812%
Volume Distribution (VD):	1.132
Pgp-substrate:	12.294032096862793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.25
CYP1A2-substrate:	0.707
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.373
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	14.327
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.124
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.281
Carcinogencity:	0.083
Eye Corrosion:	0.631
Eye Irritation:	0.939
Respiratory Toxicity:	0.293

Download Data

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

Natural Product: NPC223451

Natural Product ID:	NPC223451
*Common Name:**	3-(2,3-Dihydroxy-3-Methylbutyl)Resveratrol
IUPAC Name:	5-[(E)-2-[3-[(2R)-2,3-dihydroxy-3-methylbutyl]-4-hydroxyphenyl]ethenyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	BPJJUNOJJPFGCB-OAJJDEHYSA-N
Standard InCHI:	InChI=1S/C19H22O5/c1-19(2,24)18(23)10-14-7-12(5-6-17(14)22)3-4-13-8-15(20)11-16(21)9-13/h3-9,11,18,20-24H,10H2,1-2H3/b4-3+/t18-/m1/s1
SMILES:	Oc1cc(/C=C/c2ccc(c(c2)C[C@H](C(O)(C)C)O)O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446319
PubChem CID:	10991144
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869218]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	bark and twigs	Tewah, Central Kalimantan, Indonesia (N 38 57.003; W 094 44.767)	1999-Oct	PMID[11858749]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217294]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	480.0	nM	PMID[497591]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	13900.0	nM	PMID[497591]

☑ 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 NPC223451 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	317
0.1-0.2	1440
0.2-0.3	3957
0.3-0.4	12105
0.4-0.5	7321
0.5-0.6	5394
0.6-0.7	8486
0.7-0.8	3124
0.8-0.85	480
0.85-0.9	59
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC43525
0.9196	High Similarity	NPC476632
0.9196	High Similarity	NPC225679
0.9196	High Similarity	NPC165770
0.9196	High Similarity	NPC4493
0.9123	High Similarity	NPC473137
0.9123	High Similarity	NPC12656
0.9107	High Similarity	NPC475018
0.9052	High Similarity	NPC277588
0.9035	High Similarity	NPC117846
0.9035	High Similarity	NPC261343
0.8957	High Similarity	NPC107240
0.8929	High Similarity	NPC63698
0.8929	High Similarity	NPC61885
0.8908	High Similarity	NPC24125
0.8898	High Similarity	NPC191866
0.8879	High Similarity	NPC474486
0.886	High Similarity	NPC308689
0.8843	High Similarity	NPC474160
0.8833	High Similarity	NPC237667
0.8824	High Similarity	NPC472071
0.8814	High Similarity	NPC9592
0.8814	High Similarity	NPC144343
0.8814	High Similarity	NPC48781
0.8783	High Similarity	NPC166995
0.8772	High Similarity	NPC44732
0.874	High Similarity	NPC474453
0.8739	High Similarity	NPC151197
0.8699	High Similarity	NPC33654
0.8689	High Similarity	NPC53567
0.8684	High Similarity	NPC19808
0.8684	High Similarity	NPC33728
0.8684	High Similarity	NPC473524
0.8678	High Similarity	NPC476633
0.8673	High Similarity	NPC61033
0.8673	High Similarity	NPC305603
0.8661	High Similarity	NPC292452
0.8661	High Similarity	NPC474839
0.864	High Similarity	NPC148366
0.864	High Similarity	NPC311293
0.8621	High Similarity	NPC473521
0.8605	High Similarity	NPC256262
0.8596	High Similarity	NPC262365
0.8596	High Similarity	NPC174981
0.8584	High Similarity	NPC39097
0.8584	High Similarity	NPC109691
0.8584	High Similarity	NPC470700
0.8584	High Similarity	NPC302681
0.8584	High Similarity	NPC39664
0.8584	High Similarity	NPC118286
0.8583	High Similarity	NPC103799
0.8583	High Similarity	NPC217174
0.8571	High Similarity	NPC320864
0.8571	High Similarity	NPC119860
0.8571	High Similarity	NPC470760
0.8571	High Similarity	NPC241891
0.8571	High Similarity	NPC30506
0.8571	High Similarity	NPC102216
0.8571	High Similarity	NPC212015
0.8547	High Similarity	NPC319803
0.8534	High Similarity	NPC179002
0.8534	High Similarity	NPC257430
0.8534	High Similarity	NPC187583
0.8534	High Similarity	NPC268032
0.8534	High Similarity	NPC224527
0.8509	High Similarity	NPC54844
0.8496	Intermediate Similarity	NPC134829
0.8496	Intermediate Similarity	NPC246056
0.8492	Intermediate Similarity	NPC274717
0.8487	Intermediate Similarity	NPC115808
0.8475	Intermediate Similarity	NPC120280
0.8468	Intermediate Similarity	NPC224342
0.8462	Intermediate Similarity	NPC473413
0.8455	Intermediate Similarity	NPC18128
0.8455	Intermediate Similarity	NPC77789
0.8448	Intermediate Similarity	NPC174096
0.8448	Intermediate Similarity	NPC147634
0.8448	Intermediate Similarity	NPC226401
0.8448	Intermediate Similarity	NPC120982
0.8448	Intermediate Similarity	NPC79793
0.8425	Intermediate Similarity	NPC170844
0.8425	Intermediate Similarity	NPC476968
0.8421	Intermediate Similarity	NPC248904
0.8413	Intermediate Similarity	NPC252131
0.8413	Intermediate Similarity	NPC242032
0.8403	Intermediate Similarity	NPC246760
0.8403	Intermediate Similarity	NPC84999
0.8397	Intermediate Similarity	NPC470802
0.8393	Intermediate Similarity	NPC91461
0.8393	Intermediate Similarity	NPC7686
0.8393	Intermediate Similarity	NPC100340
0.8393	Intermediate Similarity	NPC143659
0.8393	Intermediate Similarity	NPC40258
0.839	Intermediate Similarity	NPC23804
0.839	Intermediate Similarity	NPC263753
0.8385	Intermediate Similarity	NPC124085
0.8385	Intermediate Similarity	NPC117048
0.8374	Intermediate Similarity	NPC39029
0.8362	Intermediate Similarity	NPC202647
0.8362	Intermediate Similarity	NPC62258
0.8362	Intermediate Similarity	NPC55617
0.8361	Intermediate Similarity	NPC475245
0.8361	Intermediate Similarity	NPC282255
0.8348	Intermediate Similarity	NPC158253
0.8348	Intermediate Similarity	NPC232523
0.8348	Intermediate Similarity	NPC204901
0.8347	Intermediate Similarity	NPC131118
0.8347	Intermediate Similarity	NPC469609
0.8346	Intermediate Similarity	NPC28765
0.8346	Intermediate Similarity	NPC87224
0.8346	Intermediate Similarity	NPC186843
0.8346	Intermediate Similarity	NPC98631
0.8346	Intermediate Similarity	NPC222572
0.8346	Intermediate Similarity	NPC206615
0.8346	Intermediate Similarity	NPC470213
0.8333	Intermediate Similarity	NPC37802
0.8333	Intermediate Similarity	NPC276212
0.8333	Intermediate Similarity	NPC138942
0.8321	Intermediate Similarity	NPC61946
0.8321	Intermediate Similarity	NPC151224
0.8321	Intermediate Similarity	NPC164787
0.832	Intermediate Similarity	NPC174729
0.832	Intermediate Similarity	NPC139774
0.8319	Intermediate Similarity	NPC249828
0.8319	Intermediate Similarity	NPC146798
0.8319	Intermediate Similarity	NPC24404
0.8319	Intermediate Similarity	NPC313030
0.8319	Intermediate Similarity	NPC71002
0.8319	Intermediate Similarity	NPC85479
0.8319	Intermediate Similarity	NPC94351
0.8319	Intermediate Similarity	NPC106396
0.8319	Intermediate Similarity	NPC222522
0.8319	Intermediate Similarity	NPC168303
0.8319	Intermediate Similarity	NPC302219
0.8319	Intermediate Similarity	NPC242342
0.8319	Intermediate Similarity	NPC53051
0.8308	Intermediate Similarity	NPC475840
0.8308	Intermediate Similarity	NPC11060
0.8308	Intermediate Similarity	NPC92805
0.8308	Intermediate Similarity	NPC85435
0.8305	Intermediate Similarity	NPC228425
0.8304	Intermediate Similarity	NPC213730
0.8304	Intermediate Similarity	NPC248573
0.8304	Intermediate Similarity	NPC10588
0.8304	Intermediate Similarity	NPC275053
0.8304	Intermediate Similarity	NPC294741
0.8304	Intermediate Similarity	NPC161571
0.8304	Intermediate Similarity	NPC166761
0.8295	Intermediate Similarity	NPC15543
0.8295	Intermediate Similarity	NPC474017
0.8291	Intermediate Similarity	NPC224870
0.8284	Intermediate Similarity	NPC263261
0.8284	Intermediate Similarity	NPC87725
0.8281	Intermediate Similarity	NPC469963
0.8281	Intermediate Similarity	NPC469951
0.8281	Intermediate Similarity	NPC134360
0.8279	Intermediate Similarity	NPC469644
0.8276	Intermediate Similarity	NPC34864
0.8276	Intermediate Similarity	NPC58427
0.8276	Intermediate Similarity	NPC105727
0.8276	Intermediate Similarity	NPC114392
0.8276	Intermediate Similarity	NPC95344
0.8271	Intermediate Similarity	NPC475836
0.8271	Intermediate Similarity	NPC32630
0.8268	Intermediate Similarity	NPC169474
0.8268	Intermediate Similarity	NPC159968
0.8268	Intermediate Similarity	NPC293054
0.8268	Intermediate Similarity	NPC236791
0.8268	Intermediate Similarity	NPC124452
0.8268	Intermediate Similarity	NPC246620
0.8268	Intermediate Similarity	NPC282000
0.8268	Intermediate Similarity	NPC82679
0.8268	Intermediate Similarity	NPC74817
0.8268	Intermediate Similarity	NPC324112
0.8264	Intermediate Similarity	NPC474933
0.8264	Intermediate Similarity	NPC69261
0.8264	Intermediate Similarity	NPC33270
0.8261	Intermediate Similarity	NPC12640
0.8261	Intermediate Similarity	NPC201662
0.8261	Intermediate Similarity	NPC99836
0.8258	Intermediate Similarity	NPC302701
0.8258	Intermediate Similarity	NPC20829
0.8258	Intermediate Similarity	NPC269091
0.8258	Intermediate Similarity	NPC474639
0.8258	Intermediate Similarity	NPC16435
0.8258	Intermediate Similarity	NPC230734
0.8258	Intermediate Similarity	NPC3049
0.8258	Intermediate Similarity	NPC18189
0.8258	Intermediate Similarity	NPC262585
0.8258	Intermediate Similarity	NPC227503
0.8258	Intermediate Similarity	NPC306441
0.8258	Intermediate Similarity	NPC472334
0.8258	Intermediate Similarity	NPC472336
0.8254	Intermediate Similarity	NPC188022
0.8254	Intermediate Similarity	NPC103420
0.8254	Intermediate Similarity	NPC17809
0.8254	Intermediate Similarity	NPC105925
0.8254	Intermediate Similarity	NPC105031
0.8254	Intermediate Similarity	NPC102540
0.8254	Intermediate Similarity	NPC285040

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 NPC223451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	852
0.2-0.3	1697
0.3-0.4	2938
0.4-0.5	1709
0.5-0.6	1104
0.6-0.7	479
0.7-0.8	77
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8425	Intermediate Similarity	NPD3027	Phase 3
0.8393	Intermediate Similarity	NPD940	Approved
0.8393	Intermediate Similarity	NPD846	Approved
0.8304	Intermediate Similarity	NPD1242	Phase 1
0.8205	Intermediate Similarity	NPD4750	Phase 3
0.8092	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1613	Approved
0.8051	Intermediate Similarity	NPD3021	Approved
0.8051	Intermediate Similarity	NPD3022	Approved
0.7969	Intermediate Similarity	NPD3094	Phase 2
0.7946	Intermediate Similarity	NPD2859	Approved
0.7946	Intermediate Similarity	NPD2860	Approved
0.7939	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3020	Approved
0.7857	Intermediate Similarity	NPD2934	Approved
0.7857	Intermediate Similarity	NPD2933	Approved
0.7795	Intermediate Similarity	NPD3092	Approved
0.7786	Intermediate Similarity	NPD4908	Phase 1
0.7786	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4625	Phase 3
0.771	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7635	Approved
0.7704	Intermediate Similarity	NPD2568	Approved
0.7656	Intermediate Similarity	NPD1610	Phase 2
0.7632	Intermediate Similarity	NPD844	Approved
0.7619	Intermediate Similarity	NPD1548	Phase 1
0.7619	Intermediate Similarity	NPD3091	Approved
0.7612	Intermediate Similarity	NPD6407	Approved
0.7612	Intermediate Similarity	NPD6405	Approved
0.7538	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD1809	Phase 2
0.7456	Intermediate Similarity	NPD845	Approved
0.7444	Intermediate Similarity	NPD2861	Phase 2
0.7438	Intermediate Similarity	NPD2342	Discontinued
0.7432	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4060	Phase 1
0.7426	Intermediate Similarity	NPD943	Approved
0.7414	Intermediate Similarity	NPD288	Approved
0.7405	Intermediate Similarity	NPD4749	Approved
0.7391	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD3095	Discontinued
0.736	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4380	Phase 2
0.7339	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3018	Phase 2
0.7299	Intermediate Similarity	NPD2238	Phase 2
0.7299	Intermediate Similarity	NPD3059	Approved
0.7299	Intermediate Similarity	NPD3061	Approved
0.7299	Intermediate Similarity	NPD3062	Approved
0.7293	Intermediate Similarity	NPD1129	Approved
0.7293	Intermediate Similarity	NPD1131	Approved
0.7293	Intermediate Similarity	NPD1133	Approved
0.7293	Intermediate Similarity	NPD1134	Approved
0.7293	Intermediate Similarity	NPD1135	Approved
0.7266	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3554	Approved
0.7266	Intermediate Similarity	NPD3552	Approved
0.7266	Intermediate Similarity	NPD3553	Approved
0.7266	Intermediate Similarity	NPD4538	Approved
0.7266	Intermediate Similarity	NPD3555	Approved
0.7266	Intermediate Similarity	NPD4536	Approved
0.7246	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5124	Phase 1
0.7244	Intermediate Similarity	NPD6671	Approved
0.7234	Intermediate Similarity	NPD7266	Discontinued
0.7231	Intermediate Similarity	NPD9381	Approved
0.7231	Intermediate Similarity	NPD9384	Approved
0.7222	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5314	Approved
0.7172	Intermediate Similarity	NPD7390	Discontinued
0.7164	Intermediate Similarity	NPD4103	Phase 2
0.7164	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2935	Discontinued
0.7153	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9622	Approved
0.7143	Intermediate Similarity	NPD4659	Approved
0.7143	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD2982	Phase 2
0.7133	Intermediate Similarity	NPD1934	Approved
0.7123	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1091	Approved
0.7113	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD859	Approved
0.7111	Intermediate Similarity	NPD599	Approved
0.7111	Intermediate Similarity	NPD602	Approved
0.7111	Intermediate Similarity	NPD858	Approved
0.7099	Intermediate Similarity	NPD4059	Approved
0.7099	Intermediate Similarity	NPD4589	Approved
0.7097	Intermediate Similarity	NPD2684	Approved
0.7092	Intermediate Similarity	NPD5960	Phase 3
0.7092	Intermediate Similarity	NPD5588	Approved
0.709	Intermediate Similarity	NPD8651	Approved
0.7087	Intermediate Similarity	NPD2234	Approved
0.7087	Intermediate Similarity	NPD2228	Approved
0.7087	Intermediate Similarity	NPD2229	Approved
0.7087	Intermediate Similarity	NPD5283	Phase 1
0.7083	Intermediate Similarity	NPD3028	Approved
0.7083	Intermediate Similarity	NPD3400	Discontinued
0.7077	Intermediate Similarity	NPD5303	Approved
0.7077	Intermediate Similarity	NPD5304	Approved
0.7068	Intermediate Similarity	NPD2561	Approved
0.7068	Intermediate Similarity	NPD2562	Approved
0.7068	Intermediate Similarity	NPD2981	Phase 2
0.7063	Intermediate Similarity	NPD228	Approved
0.7063	Intermediate Similarity	NPD2424	Discontinued
0.7054	Intermediate Similarity	NPD111	Approved
0.705	Intermediate Similarity	NPD1555	Discontinued
0.704	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6190	Approved
0.7031	Intermediate Similarity	NPD497	Approved
0.7023	Intermediate Similarity	NPD4093	Discontinued
0.702	Intermediate Similarity	NPD37	Approved
0.7016	Intermediate Similarity	NPD290	Approved
0.7008	Intermediate Similarity	NPD7843	Approved
0.6992	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD422	Phase 1
0.6992	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5058	Phase 3
0.6985	Remote Similarity	NPD9621	Approved
0.6985	Remote Similarity	NPD9619	Approved
0.6985	Remote Similarity	NPD9620	Approved
0.6984	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7157	Approved
0.6972	Remote Similarity	NPD1510	Phase 2
0.697	Remote Similarity	NPD2286	Discontinued
0.697	Remote Similarity	NPD5125	Phase 3
0.697	Remote Similarity	NPD3019	Approved
0.697	Remote Similarity	NPD2932	Approved
0.697	Remote Similarity	NPD4626	Approved
0.697	Remote Similarity	NPD5126	Approved
0.6967	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD496	Approved
0.6953	Remote Similarity	NPD498	Approved
0.6953	Remote Similarity	NPD495	Approved
0.6948	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7075	Discontinued
0.6947	Remote Similarity	NPD7741	Discontinued
0.6939	Remote Similarity	NPD7212	Phase 2
0.6939	Remote Similarity	NPD7213	Phase 3
0.6934	Remote Similarity	NPD5736	Approved
0.6929	Remote Similarity	NPD3620	Phase 2
0.6929	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1240	Approved
0.6923	Remote Similarity	NPD5408	Approved
0.6923	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5404	Approved
0.6923	Remote Similarity	NPD5406	Approved
0.6923	Remote Similarity	NPD5405	Approved
0.6906	Remote Similarity	NPD601	Approved
0.6906	Remote Similarity	NPD598	Approved
0.6906	Remote Similarity	NPD597	Approved
0.6905	Remote Similarity	NPD1792	Phase 2
0.6903	Remote Similarity	NPD6234	Discontinued
0.6899	Remote Similarity	NPD9614	Approved
0.6899	Remote Similarity	NPD6166	Phase 2
0.6899	Remote Similarity	NPD9618	Approved
0.6899	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1652	Phase 2
0.6892	Remote Similarity	NPD7447	Phase 1
0.6892	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4966	Approved
0.6883	Remote Similarity	NPD4967	Phase 2
0.6883	Remote Similarity	NPD4965	Approved
0.6883	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD230	Phase 1
0.6879	Remote Similarity	NPD5735	Approved
0.6875	Remote Similarity	NPD5762	Approved
0.6875	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5763	Approved
0.687	Remote Similarity	NPD16	Approved
0.687	Remote Similarity	NPD856	Approved
0.6867	Remote Similarity	NPD1653	Approved
0.6866	Remote Similarity	NPD1201	Approved
0.6863	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2801	Approved
0.6861	Remote Similarity	NPD6584	Phase 3
0.6857	Remote Similarity	NPD1130	Approved
0.6857	Remote Similarity	NPD1136	Approved
0.6857	Remote Similarity	NPD1132	Approved
0.6853	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6559	Discontinued
0.6849	Remote Similarity	NPD3892	Phase 2
0.6842	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6696	Suspended
0.6831	Remote Similarity	NPD1607	Approved
0.6831	Remote Similarity	NPD823	Approved
0.6831	Remote Similarity	NPD817	Approved
0.6831	Remote Similarity	NPD4097	Suspended
0.6828	Remote Similarity	NPD1549	Phase 2

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