NPASS Compound

Structure

NPC221318 OpenBabel07101718292D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -3.3090 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 4.4152 -1.3090 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 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 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 2.6831 -0.3090 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 0.0000 -1.6180 0.0000 C 0 0 1 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 1.8171 0.1910 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 -0.5878 -0.8090 0.0000 C 0 0 1 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 -0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 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 1.8171 1.1910 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 10 2 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 6 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 1 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.13
Volume:	307.688
LogP:	2.504
LogD:	2.464
LogS:	-3.021
# Rotatable Bonds:	3
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.911
Synthetic Accessibility Score:	3.518
Fsp3:	0.412
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	4.32915439887438e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.943
Plasma Protein Binding (PPB):	72.96857452392578%
Volume Distribution (VD):	1.348
Pgp-substrate:	16.91927719116211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.297
CYP1A2-substrate:	0.767
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.801
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.06
CYP3A4-substrate:	0.452

ADMET: Excretion

Clearance (CL):	7.227
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.389
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.222
Carcinogencity:	0.26
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC221318

Natural Product ID:	NPC221318
*Common Name:**	Avicenol A
IUPAC Name:	(2S,3S)-2-(2-hydroxypropan-2-yl)-4,9-dimethoxy-2,3-dihydrobenzo[f][1]benzofuran-3-ol
Synonyms:
Standard InCHIKey:	ZIFQTGAHILVMCO-LRDDRELGSA-N
Standard InCHI:	InChI=1S/C17H20O5/c1-17(2,19)16-12(18)11-13(20-3)9-7-5-6-8-10(9)14(21-4)15(11)22-16/h5-8,12,16,18-19H,1-4H3/t12-,16-/m0/s1
SMILES:	COc1c2ccccc2c(c2c1O[C@@H]([C@H]2O)C(O)(C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375894
PubChem CID:	11208912
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO3629	Avicennia marina	Species	Acanthaceae	Eukaryota	twigs	n.a.	n.a.	PMID[17500572]
NPO3629	Avicennia marina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19377635]
NPO3629	Avicennia marina	Species	Acanthaceae	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
GI50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	GI50	>	10.0	ug.mL-1	PMID[533119]
NPT111	Cell Line	K562	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[533119]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	>	10.0	ug.mL-1	PMID[533119]

☑ 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 NPC221318 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	472
0.1-0.2	1652
0.2-0.3	4380
0.3-0.4	11655
0.4-0.5	6802
0.5-0.6	4215
0.6-0.7	7455
0.7-0.8	4962
0.8-0.85	713
0.85-0.9	362
0.9-0.95	27
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9854	High Similarity	NPC258083
0.9291	High Similarity	NPC477616
0.9247	High Similarity	NPC160196
0.9209	High Similarity	NPC477938
0.9167	High Similarity	NPC474397
0.9149	High Similarity	NPC263261
0.9149	High Similarity	NPC87725
0.9122	High Similarity	NPC80918
0.9122	High Similarity	NPC188578
0.9097	High Similarity	NPC233980
0.9091	High Similarity	NPC50250
0.9091	High Similarity	NPC45257
0.9091	High Similarity	NPC93323
0.9091	High Similarity	NPC12641
0.9091	High Similarity	NPC280092
0.9078	High Similarity	NPC160283
0.9078	High Similarity	NPC254759
0.9034	High Similarity	NPC101376
0.9034	High Similarity	NPC21776
0.9034	High Similarity	NPC16269
0.9028	High Similarity	NPC469557
0.9021	High Similarity	NPC102044
0.9021	High Similarity	NPC474104
0.9021	High Similarity	NPC85264
0.9021	High Similarity	NPC47633
0.9014	High Similarity	NPC311530
0.9014	High Similarity	NPC265075
0.9007	High Similarity	NPC292882
0.9	High Similarity	NPC327735
0.9	High Similarity	NPC126101
0.9	High Similarity	NPC472336
0.9	High Similarity	NPC472334
0.8993	High Similarity	NPC16485
0.898	High Similarity	NPC158784
0.8958	High Similarity	NPC63879
0.8951	High Similarity	NPC175838
0.8951	High Similarity	NPC107161
0.8944	High Similarity	NPC27495
0.8929	High Similarity	NPC256262
0.8929	High Similarity	NPC472337
0.8929	High Similarity	NPC134968
0.8921	High Similarity	NPC26394
0.8919	High Similarity	NPC2745
0.8919	High Similarity	NPC302915
0.8897	High Similarity	NPC181615
0.8881	High Similarity	NPC247291
0.8881	High Similarity	NPC471389
0.8873	High Similarity	NPC471388
0.8873	High Similarity	NPC79622
0.8873	High Similarity	NPC29868
0.8873	High Similarity	NPC212942
0.8873	High Similarity	NPC32630
0.8865	High Similarity	NPC54743
0.8865	High Similarity	NPC29799
0.8865	High Similarity	NPC476698
0.8865	High Similarity	NPC205442
0.8865	High Similarity	NPC263367
0.8865	High Similarity	NPC156502
0.8865	High Similarity	NPC177160
0.8865	High Similarity	NPC209985
0.8865	High Similarity	NPC10737
0.8865	High Similarity	NPC477939
0.8859	High Similarity	NPC325860
0.8859	High Similarity	NPC157783
0.8851	High Similarity	NPC195561
0.8849	High Similarity	NPC230219
0.8844	High Similarity	NPC212142
0.8844	High Similarity	NPC473876
0.8836	High Similarity	NPC260397
0.8836	High Similarity	NPC112251
0.8828	High Similarity	NPC469795
0.8828	High Similarity	NPC473845
0.8828	High Similarity	NPC473108
0.8819	High Similarity	NPC41782
0.8811	High Similarity	NPC184797
0.8811	High Similarity	NPC73505
0.8811	High Similarity	NPC308768
0.8811	High Similarity	NPC295719
0.8811	High Similarity	NPC34431
0.8811	High Similarity	NPC12668
0.8811	High Similarity	NPC309124
0.8811	High Similarity	NPC165026
0.8811	High Similarity	NPC259519
0.8803	High Similarity	NPC102904
0.8803	High Similarity	NPC107551
0.8803	High Similarity	NPC474282
0.8803	High Similarity	NPC176051
0.8803	High Similarity	NPC56329
0.8803	High Similarity	NPC242715
0.8803	High Similarity	NPC266006
0.8803	High Similarity	NPC103976
0.8803	High Similarity	NPC326797
0.8794	High Similarity	NPC61946
0.8786	High Similarity	NPC263064
0.8786	High Similarity	NPC475840
0.8776	High Similarity	NPC116019
0.8768	High Similarity	NPC226788
0.8768	High Similarity	NPC210623
0.8768	High Similarity	NPC285339
0.8768	High Similarity	NPC273295
0.8768	High Similarity	NPC218856
0.8768	High Similarity	NPC202582
0.8768	High Similarity	NPC222004
0.8768	High Similarity	NPC190629
0.8768	High Similarity	NPC3439
0.8768	High Similarity	NPC470258
0.8759	High Similarity	NPC469386
0.8741	High Similarity	NPC25966
0.8741	High Similarity	NPC319647
0.8741	High Similarity	NPC105847
0.8741	High Similarity	NPC220344
0.8741	High Similarity	NPC218131
0.8741	High Similarity	NPC275061
0.8741	High Similarity	NPC473739
0.8741	High Similarity	NPC243996
0.8741	High Similarity	NPC236306
0.8741	High Similarity	NPC132804
0.8741	High Similarity	NPC70682
0.8741	High Similarity	NPC260741
0.8741	High Similarity	NPC232164
0.8741	High Similarity	NPC245207
0.8741	High Similarity	NPC184613
0.8741	High Similarity	NPC243759
0.8741	High Similarity	NPC127218
0.8733	High Similarity	NPC474442
0.8732	High Similarity	NPC173660
0.8732	High Similarity	NPC30632
0.8732	High Similarity	NPC306441
0.8732	High Similarity	NPC143139
0.8732	High Similarity	NPC230734
0.8732	High Similarity	NPC16435
0.8732	High Similarity	NPC202846
0.8732	High Similarity	NPC269091
0.8732	High Similarity	NPC234952
0.8732	High Similarity	NPC470802
0.8732	High Similarity	NPC302701
0.8732	High Similarity	NPC227503
0.8732	High Similarity	NPC474639
0.8723	High Similarity	NPC287745
0.8723	High Similarity	NPC474478
0.8723	High Similarity	NPC187616
0.8723	High Similarity	NPC117048
0.8723	High Similarity	NPC193026
0.8723	High Similarity	NPC49603
0.8723	High Similarity	NPC310854
0.8723	High Similarity	NPC124085
0.8716	High Similarity	NPC473408
0.8714	High Similarity	NPC18842
0.8707	High Similarity	NPC162193
0.8705	High Similarity	NPC470727
0.869	High Similarity	NPC475891
0.869	High Similarity	NPC470917
0.869	High Similarity	NPC2613
0.869	High Similarity	NPC59841
0.869	High Similarity	NPC204347
0.8671	High Similarity	NPC200935
0.8671	High Similarity	NPC266453
0.8671	High Similarity	NPC90615
0.8671	High Similarity	NPC272157
0.8671	High Similarity	NPC276490
0.8671	High Similarity	NPC35550
0.8671	High Similarity	NPC201145
0.8671	High Similarity	NPC3072
0.8671	High Similarity	NPC46277
0.8671	High Similarity	NPC22902
0.8671	High Similarity	NPC151656
0.8671	High Similarity	NPC73535
0.8671	High Similarity	NPC156948
0.8671	High Similarity	NPC25111
0.8671	High Similarity	NPC230919
0.8671	High Similarity	NPC6262
0.8671	High Similarity	NPC301765
0.8671	High Similarity	NPC86605
0.8662	High Similarity	NPC234333
0.8662	High Similarity	NPC158142
0.8662	High Similarity	NPC47398
0.8662	High Similarity	NPC111655
0.8662	High Similarity	NPC121812
0.8662	High Similarity	NPC201357
0.8662	High Similarity	NPC473413
0.8662	High Similarity	NPC200557
0.8662	High Similarity	NPC260898
0.8662	High Similarity	NPC10314
0.8662	High Similarity	NPC69029
0.8662	High Similarity	NPC164787
0.8662	High Similarity	NPC281521
0.8662	High Similarity	NPC255147
0.8662	High Similarity	NPC470356
0.8662	High Similarity	NPC94750
0.8662	High Similarity	NPC195022
0.8662	High Similarity	NPC108198
0.8662	High Similarity	NPC241241
0.8662	High Similarity	NPC474206
0.8662	High Similarity	NPC112939
0.8662	High Similarity	NPC294884
0.8662	High Similarity	NPC112246
0.8662	High Similarity	NPC151224
0.8652	High Similarity	NPC105554
0.8652	High Similarity	NPC158331
0.8652	High Similarity	NPC269528

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 NPC221318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	908
0.2-0.3	1912
0.3-0.4	2783
0.4-0.5	1577
0.5-0.6	889
0.6-0.7	566
0.7-0.8	116
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD3027	Phase 3
0.8451	Intermediate Similarity	NPD1613	Approved
0.8451	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD4625	Phase 3
0.821	Intermediate Similarity	NPD5844	Phase 1
0.8169	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6674	Discontinued
0.8121	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD37	Approved
0.7931	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4966	Approved
0.7925	Intermediate Similarity	NPD4967	Phase 2
0.7925	Intermediate Similarity	NPD4965	Approved
0.7887	Intermediate Similarity	NPD6696	Suspended
0.7847	Intermediate Similarity	NPD2861	Phase 2
0.7826	Intermediate Similarity	NPD6234	Discontinued
0.7808	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4908	Phase 1
0.773	Intermediate Similarity	NPD7199	Phase 2
0.7703	Intermediate Similarity	NPD4060	Phase 1
0.7692	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4749	Approved
0.7688	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1610	Phase 2
0.7669	Intermediate Similarity	NPD5494	Approved
0.7655	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1934	Approved
0.7605	Intermediate Similarity	NPD7228	Approved
0.7603	Intermediate Similarity	NPD3018	Phase 2
0.7595	Intermediate Similarity	NPD1653	Approved
0.7584	Intermediate Similarity	NPD3620	Phase 2
0.7584	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2801	Approved
0.7576	Intermediate Similarity	NPD6232	Discontinued
0.7552	Intermediate Similarity	NPD3705	Approved
0.753	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1548	Phase 1
0.7516	Intermediate Similarity	NPD5762	Approved
0.7516	Intermediate Similarity	NPD5763	Approved
0.7485	Intermediate Similarity	NPD3882	Suspended
0.7468	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2983	Phase 2
0.7448	Intermediate Similarity	NPD2982	Phase 2
0.744	Intermediate Similarity	NPD7473	Discontinued
0.7431	Intermediate Similarity	NPD1611	Approved
0.7427	Intermediate Similarity	NPD6559	Discontinued
0.7417	Intermediate Similarity	NPD5735	Approved
0.7417	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5124	Phase 1
0.7413	Intermediate Similarity	NPD5126	Approved
0.7413	Intermediate Similarity	NPD5125	Phase 3
0.741	Intermediate Similarity	NPD1398	Phase 1
0.741	Intermediate Similarity	NPD5283	Phase 1
0.7397	Intermediate Similarity	NPD8651	Approved
0.7396	Intermediate Similarity	NPD3818	Discontinued
0.7389	Intermediate Similarity	NPD5058	Phase 3
0.7386	Intermediate Similarity	NPD5588	Approved
0.7381	Intermediate Similarity	NPD6166	Phase 2
0.7381	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2981	Phase 2
0.7376	Intermediate Similarity	NPD7340	Approved
0.7372	Intermediate Similarity	NPD3892	Phase 2
0.7362	Intermediate Similarity	NPD5929	Approved
0.7333	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7240	Approved
0.7325	Intermediate Similarity	NPD2677	Approved
0.7321	Intermediate Similarity	NPD2969	Approved
0.7321	Intermediate Similarity	NPD2970	Approved
0.732	Intermediate Similarity	NPD4538	Approved
0.732	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4536	Approved
0.7317	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2563	Approved
0.7317	Intermediate Similarity	NPD2560	Approved
0.7314	Intermediate Similarity	NPD4663	Approved
0.731	Intermediate Similarity	NPD1091	Approved
0.7305	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD6671	Approved
0.7296	Intermediate Similarity	NPD2533	Approved
0.7296	Intermediate Similarity	NPD2534	Approved
0.7296	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD7906	Approved
0.7273	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7262	Intermediate Similarity	NPD3051	Approved
0.7244	Intermediate Similarity	NPD2424	Discontinued
0.7229	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6100	Approved
0.7226	Intermediate Similarity	NPD6099	Approved
0.7222	Intermediate Similarity	NPD4005	Discontinued
0.7222	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7985	Registered
0.7219	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7635	Approved
0.7212	Intermediate Similarity	NPD3817	Phase 2
0.7209	Intermediate Similarity	NPD7074	Phase 3
0.7202	Intermediate Similarity	NPD1247	Approved
0.7188	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7549	Discontinued
0.7183	Intermediate Similarity	NPD7157	Approved
0.7178	Intermediate Similarity	NPD4675	Approved
0.7178	Intermediate Similarity	NPD4678	Approved
0.7178	Intermediate Similarity	NPD4380	Phase 2
0.7176	Intermediate Similarity	NPD2489	Approved
0.7176	Intermediate Similarity	NPD27	Approved
0.7174	Intermediate Similarity	NPD2684	Approved
0.7172	Intermediate Similarity	NPD4626	Approved
0.7161	Intermediate Similarity	NPD5960	Phase 3
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6331	Phase 2
0.7151	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7313	Approved
0.7143	Intermediate Similarity	NPD4578	Approved
0.7143	Intermediate Similarity	NPD7311	Approved
0.7143	Intermediate Similarity	NPD4666	Phase 3
0.7143	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD7312	Approved
0.7143	Intermediate Similarity	NPD4097	Suspended
0.7143	Intermediate Similarity	NPD4577	Approved
0.7143	Intermediate Similarity	NPD7310	Approved
0.7125	Intermediate Similarity	NPD1511	Approved
0.7124	Intermediate Similarity	NPD4140	Approved
0.7124	Intermediate Similarity	NPD2238	Phase 2
0.711	Intermediate Similarity	NPD7472	Approved
0.7103	Intermediate Similarity	NPD1357	Approved
0.7103	Intermediate Similarity	NPD5691	Approved
0.7102	Intermediate Similarity	NPD7309	Approved
0.7101	Intermediate Similarity	NPD290	Approved
0.7095	Intermediate Similarity	NPD5327	Phase 3
0.7093	Intermediate Similarity	NPD3751	Discontinued
0.7092	Intermediate Similarity	NPD7843	Approved
0.7089	Intermediate Similarity	NPD1652	Phase 2
0.7089	Intermediate Similarity	NPD4237	Approved
0.7089	Intermediate Similarity	NPD4236	Phase 3
0.7086	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5709	Phase 3
0.7081	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6355	Discontinued
0.707	Intermediate Similarity	NPD1375	Discontinued
0.707	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3540	Phase 1
0.707	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6004	Phase 3
0.707	Intermediate Similarity	NPD6002	Phase 3
0.707	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6005	Phase 3
0.7066	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6071	Discontinued
0.7048	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4110	Phase 3
0.7039	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1512	Approved
0.7032	Intermediate Similarity	NPD6353	Approved
0.703	Intermediate Similarity	NPD6072	Discontinued
0.7024	Intermediate Similarity	NPD4055	Discovery
0.7024	Intermediate Similarity	NPD7075	Discontinued
0.7013	Intermediate Similarity	NPD1558	Phase 1
0.7012	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2438	Suspended
0.7006	Intermediate Similarity	NPD5402	Approved
0.7006	Intermediate Similarity	NPD3539	Phase 1
0.7	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD3094	Phase 2
0.6989	Remote Similarity	NPD7808	Phase 3
0.6988	Remote Similarity	NPD6801	Discontinued
0.6986	Remote Similarity	NPD1651	Approved
0.6982	Remote Similarity	NPD919	Approved
0.6981	Remote Similarity	NPD5177	Phase 3
0.698	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6797	Phase 2
0.697	Remote Similarity	NPD6599	Discontinued
0.6968	Remote Similarity	NPD3657	Discovery
0.6959	Remote Similarity	NPD422	Phase 1
0.6948	Remote Similarity	NPD6233	Phase 2
0.6946	Remote Similarity	NPD8455	Phase 2
0.6943	Remote Similarity	NPD2155	Approved
0.6943	Remote Similarity	NPD7033	Discontinued
0.6943	Remote Similarity	NPD2154	Approved
0.6943	Remote Similarity	NPD2156	Approved
0.6937	Remote Similarity	NPD3750	Approved
0.6937	Remote Similarity	NPD7466	Approved
0.6933	Remote Similarity	NPD1283	Approved
0.6933	Remote Similarity	NPD6090	Discontinued
0.6933	Remote Similarity	NPD2676	Approved
0.6933	Remote Similarity	NPD2675	Approved
0.6933	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7251	Discontinued
0.6928	Remote Similarity	NPD7095	Approved
0.6928	Remote Similarity	NPD7615	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data