NPASS Compound

Structure

NPC476394 OpenBabel07101718292D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.3301 1.5000 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 2.5981 1.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 -1.7321 2.0000 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 2.5981 0.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 22 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 23 1 0 0 0 0 13 22 1 0 0 0 0 14 24 1 0 0 0 0 15 8 1 1 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 9 1 6 0 0 0 16 24 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.09
Volume:	319.995
LogP:	2.159
LogD:	1.421
LogS:	-3.262
# Rotatable Bonds:	4
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.786
Synthetic Accessibility Score:	3.012
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.891
MDCK Permeability:	8.043473826546688e-06
Pgp-inhibitor:	0.451
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	91.02799987792969%
Volume Distribution (VD):	0.416
Pgp-substrate:	10.867547988891602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	2.72
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.367
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.036
Carcinogencity:	0.844
Eye Corrosion:	0.003
Eye Irritation:	0.049
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC476394

Natural Product ID:	NPC476394
*Common Name:**	3-O-Methyl Isoamericanoic Acid A
IUPAC Name:	(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid
Synonyms:
Standard InCHIKey:	HMMMZZGULXPBRP-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C17H16O7/c1-22-13-6-9(2-4-11(13)19)16-15(8-18)23-12-5-3-10(17(20)21)7-14(12)24-16/h2-7,15-16,18-19H,8H2,1H3,(H,20,21)/t15-,16-/m1/s1
SMILES:	COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C(=O)O)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL594777
PubChem CID:	46226513
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002699] Benzodioxanes [CHEMONTID:0002704] Phenylbenzodioxanes [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17907781]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[19646881]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	1.7	n.a.	PMID[502435]

☑ 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 NPC476394 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	327
0.1-0.2	1427
0.2-0.3	3774
0.3-0.4	8206
0.4-0.5	9812
0.5-0.6	3493
0.6-0.7	5399
0.7-0.8	7733
0.8-0.85	2040
0.85-0.9	432
0.9-0.95	46
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC98809
0.9789	High Similarity	NPC472969
0.9645	High Similarity	NPC473090
0.9527	High Similarity	NPC471405
0.9524	High Similarity	NPC191046
0.9524	High Similarity	NPC327032
0.9524	High Similarity	NPC194095
0.9521	High Similarity	NPC75695
0.951	High Similarity	NPC287495
0.951	High Similarity	NPC9370
0.9459	High Similarity	NPC10205
0.9433	High Similarity	NPC326065
0.9388	High Similarity	NPC134905
0.9388	High Similarity	NPC36130
0.9384	High Similarity	NPC473091
0.9338	High Similarity	NPC239966
0.9338	High Similarity	NPC203020
0.9333	High Similarity	NPC133984
0.9324	High Similarity	NPC137813
0.9324	High Similarity	NPC157898
0.9272	High Similarity	NPC160780
0.9272	High Similarity	NPC289811
0.9262	High Similarity	NPC469888
0.922	High Similarity	NPC126206
0.9211	High Similarity	NPC53889
0.9205	High Similarity	NPC226759
0.9205	High Similarity	NPC472860
0.9205	High Similarity	NPC1913
0.9189	High Similarity	NPC243891
0.9184	High Similarity	NPC111785
0.9172	High Similarity	NPC469683
0.915	High Similarity	NPC472859
0.915	High Similarity	NPC25389
0.915	High Similarity	NPC311803
0.9149	High Similarity	NPC471665
0.9149	High Similarity	NPC471664
0.9145	High Similarity	NPC87317
0.9128	High Similarity	NPC267091
0.9122	High Similarity	NPC205054
0.9103	High Similarity	NPC469615
0.9091	High Similarity	NPC33298
0.9091	High Similarity	NPC285108
0.9085	High Similarity	NPC166277
0.9085	High Similarity	NPC24164
0.9085	High Similarity	NPC476373
0.9085	High Similarity	NPC119125
0.9079	High Similarity	NPC289322
0.9079	High Similarity	NPC68324
0.9079	High Similarity	NPC160512
0.9079	High Similarity	NPC114179
0.9079	High Similarity	NPC38779
0.9079	High Similarity	NPC156818
0.9073	High Similarity	NPC145425
0.9067	High Similarity	NPC44730
0.902	High Similarity	NPC287872
0.902	High Similarity	NPC74319
0.9013	High Similarity	NPC104983
0.9013	High Similarity	NPC300845
0.9013	High Similarity	NPC291948
0.9013	High Similarity	NPC88803
0.9013	High Similarity	NPC250436
0.8981	High Similarity	NPC116745
0.898	High Similarity	NPC98356
0.8974	High Similarity	NPC142614
0.8973	High Similarity	NPC226738
0.8973	High Similarity	NPC22176
0.8973	High Similarity	NPC190587
0.8973	High Similarity	NPC121573
0.8968	High Similarity	NPC476372
0.8968	High Similarity	NPC476371
0.8961	High Similarity	NPC24627
0.8961	High Similarity	NPC289346
0.8947	High Similarity	NPC300757
0.8947	High Similarity	NPC180901
0.894	High Similarity	NPC105827
0.894	High Similarity	NPC295646
0.894	High Similarity	NPC257648
0.894	High Similarity	NPC477231
0.894	High Similarity	NPC474656
0.894	High Similarity	NPC310661
0.8936	High Similarity	NPC283823
0.8936	High Similarity	NPC159418
0.8933	High Similarity	NPC300329
0.8926	High Similarity	NPC107636
0.8903	High Similarity	NPC469889
0.8889	High Similarity	NPC318432
0.8889	High Similarity	NPC472916
0.8882	High Similarity	NPC18727
0.8874	High Similarity	NPC163883
0.8874	High Similarity	NPC93498
0.8874	High Similarity	NPC31363
0.8873	High Similarity	NPC135127
0.8867	High Similarity	NPC221091
0.8867	High Similarity	NPC259576
0.8865	High Similarity	NPC111888
0.8851	High Similarity	NPC291153
0.8846	High Similarity	NPC4013
0.8846	High Similarity	NPC148273
0.8846	High Similarity	NPC90905
0.8844	High Similarity	NPC160378
0.8844	High Similarity	NPC134975
0.8844	High Similarity	NPC239608
0.8844	High Similarity	NPC46161
0.8831	High Similarity	NPC210084
0.8831	High Similarity	NPC472598
0.8831	High Similarity	NPC99597
0.8831	High Similarity	NPC52530
0.8831	High Similarity	NPC162869
0.8831	High Similarity	NPC48208
0.8831	High Similarity	NPC474055
0.8831	High Similarity	NPC299520
0.8831	High Similarity	NPC129684
0.8831	High Similarity	NPC474208
0.8831	High Similarity	NPC470402
0.8831	High Similarity	NPC474836
0.8831	High Similarity	NPC475267
0.8831	High Similarity	NPC291508
0.8831	High Similarity	NPC156057
0.8831	High Similarity	NPC108456
0.8828	High Similarity	NPC288452
0.8828	High Similarity	NPC289690
0.8824	High Similarity	NPC2928
0.8816	High Similarity	NPC146277
0.8816	High Similarity	NPC19380
0.8816	High Similarity	NPC39732
0.8816	High Similarity	NPC302950
0.8816	High Similarity	NPC219582
0.8816	High Similarity	NPC60972
0.8816	High Similarity	NPC236637
0.8816	High Similarity	NPC131121
0.8811	High Similarity	NPC214729
0.8808	High Similarity	NPC140151
0.8805	High Similarity	NPC197708
0.8805	High Similarity	NPC658
0.88	High Similarity	NPC478242
0.8797	High Similarity	NPC13481
0.8797	High Similarity	NPC207575
0.879	High Similarity	NPC124038
0.879	High Similarity	NPC45943
0.879	High Similarity	NPC88043
0.8784	High Similarity	NPC113397
0.8782	High Similarity	NPC103201
0.8782	High Similarity	NPC349525
0.8782	High Similarity	NPC308992
0.8782	High Similarity	NPC112418
0.8782	High Similarity	NPC473106
0.8776	High Similarity	NPC478239
0.8767	High Similarity	NPC100675
0.8766	High Similarity	NPC291878
0.8766	High Similarity	NPC278778
0.8766	High Similarity	NPC255106
0.8766	High Similarity	NPC326037
0.8766	High Similarity	NPC35038
0.8766	High Similarity	NPC470896
0.8766	High Similarity	NPC320825
0.8766	High Similarity	NPC235165
0.8766	High Similarity	NPC473275
0.8766	High Similarity	NPC195796
0.8766	High Similarity	NPC227062
0.8766	High Similarity	NPC13858
0.8759	High Similarity	NPC284409
0.8758	High Similarity	NPC175230
0.8758	High Similarity	NPC25127
0.8758	High Similarity	NPC116850
0.8758	High Similarity	NPC88560
0.8758	High Similarity	NPC144801
0.8758	High Similarity	NPC472915
0.8758	High Similarity	NPC197188
0.8758	High Similarity	NPC43872
0.8758	High Similarity	NPC316539
0.8758	High Similarity	NPC238672
0.8758	High Similarity	NPC291510
0.8758	High Similarity	NPC172033
0.875	High Similarity	NPC204937
0.875	High Similarity	NPC149011
0.875	High Similarity	NPC289438
0.8742	High Similarity	NPC473818
0.8742	High Similarity	NPC298847
0.8742	High Similarity	NPC306343
0.8741	High Similarity	NPC249791
0.8741	High Similarity	NPC144662
0.8741	High Similarity	NPC237594
0.8741	High Similarity	NPC119060
0.8741	High Similarity	NPC476387
0.8734	High Similarity	NPC471788
0.8734	High Similarity	NPC165720
0.8733	High Similarity	NPC120621
0.8733	High Similarity	NPC248257
0.8733	High Similarity	NPC294972
0.8733	High Similarity	NPC142528
0.8726	High Similarity	NPC472964
0.8726	High Similarity	NPC476247
0.8726	High Similarity	NPC41009
0.8726	High Similarity	NPC474034
0.8726	High Similarity	NPC474033
0.8726	High Similarity	NPC471745
0.8725	High Similarity	NPC262282
0.8725	High Similarity	NPC30890
0.8725	High Similarity	NPC287275
0.8723	High Similarity	NPC285776

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 NPC476394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	839
0.2-0.3	1720
0.3-0.4	2476
0.4-0.5	1903
0.5-0.6	1067
0.6-0.7	647
0.7-0.8	167
0.8-0.85	27
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9013	High Similarity	NPD4868	Clinical (unspecified phase)
0.8816	High Similarity	NPD1934	Approved
0.8707	High Similarity	NPD4628	Phase 3
0.8636	High Similarity	NPD2393	Clinical (unspecified phase)
0.8636	High Similarity	NPD2801	Approved
0.8526	High Similarity	NPD3882	Suspended
0.8523	High Similarity	NPD6190	Approved
0.8509	High Similarity	NPD3818	Discontinued
0.85	High Similarity	NPD6166	Phase 2
0.85	High Similarity	NPD6167	Clinical (unspecified phase)
0.85	High Similarity	NPD6168	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3817	Phase 2
0.8457	Intermediate Similarity	NPD7054	Approved
0.8457	Intermediate Similarity	NPD5844	Phase 1
0.8415	Intermediate Similarity	NPD7685	Pre-registration
0.8414	Intermediate Similarity	NPD230	Phase 1
0.8405	Intermediate Similarity	NPD7074	Phase 3
0.8405	Intermediate Similarity	NPD7472	Approved
0.8397	Intermediate Similarity	NPD1465	Phase 2
0.8289	Intermediate Similarity	NPD1511	Approved
0.8289	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD9494	Approved
0.8242	Intermediate Similarity	NPD6797	Phase 2
0.8239	Intermediate Similarity	NPD7075	Discontinued
0.8193	Intermediate Similarity	NPD7251	Discontinued
0.8182	Intermediate Similarity	NPD1512	Approved
0.8165	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7808	Phase 3
0.8133	Intermediate Similarity	NPD7266	Discontinued
0.8125	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD4380	Phase 2
0.8052	Intermediate Similarity	NPD6799	Approved
0.8041	Intermediate Similarity	NPD447	Suspended
0.8038	Intermediate Similarity	NPD6386	Approved
0.8038	Intermediate Similarity	NPD6385	Approved
0.8037	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD5494	Approved
0.8014	Intermediate Similarity	NPD3027	Phase 3
0.8013	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5402	Approved
0.7987	Intermediate Similarity	NPD6801	Discontinued
0.7973	Intermediate Similarity	NPD1613	Approved
0.7973	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1653	Approved
0.7961	Intermediate Similarity	NPD1549	Phase 2
0.7937	Intermediate Similarity	NPD7819	Suspended
0.7905	Intermediate Similarity	NPD6233	Phase 2
0.7895	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7473	Discontinued
0.787	Intermediate Similarity	NPD7039	Approved
0.787	Intermediate Similarity	NPD7038	Approved
0.7853	Intermediate Similarity	NPD6234	Discontinued
0.7838	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD7411	Suspended
0.7801	Intermediate Similarity	NPD9545	Approved
0.78	Intermediate Similarity	NPD1933	Approved
0.7785	Intermediate Similarity	NPD5403	Approved
0.7778	Intermediate Similarity	NPD5353	Approved
0.7778	Intermediate Similarity	NPD1608	Approved
0.7771	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7764	Intermediate Similarity	NPD37	Approved
0.7759	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.775	Intermediate Similarity	NPD6599	Discontinued
0.7742	Intermediate Similarity	NPD3750	Approved
0.7738	Intermediate Similarity	NPD7228	Approved
0.773	Intermediate Similarity	NPD4966	Approved
0.773	Intermediate Similarity	NPD4967	Phase 2
0.773	Intermediate Similarity	NPD4965	Approved
0.7718	Intermediate Similarity	NPD6798	Discontinued
0.7712	Intermediate Similarity	NPD2796	Approved
0.7703	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3455	Phase 2
0.7665	Intermediate Similarity	NPD5242	Approved
0.7658	Intermediate Similarity	NPD5401	Approved
0.7655	Intermediate Similarity	NPD9269	Phase 2
0.7651	Intermediate Similarity	NPD8127	Discontinued
0.7647	Intermediate Similarity	NPD7033	Discontinued
0.7647	Intermediate Similarity	NPD1510	Phase 2
0.7635	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4110	Phase 3
0.7628	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6273	Approved
0.76	Intermediate Similarity	NPD3764	Approved
0.7597	Intermediate Similarity	NPD1551	Phase 2
0.7578	Intermediate Similarity	NPD3226	Approved
0.7578	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD8313	Approved
0.7572	Intermediate Similarity	NPD8312	Approved
0.7569	Intermediate Similarity	NPD17	Approved
0.7566	Intermediate Similarity	NPD6355	Discontinued
0.7561	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4062	Phase 3
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7543	Intermediate Similarity	NPD8434	Phase 2
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.753	Intermediate Similarity	NPD919	Approved
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7515	Intermediate Similarity	NPD7768	Phase 2
0.7515	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7483	Intermediate Similarity	NPD5536	Phase 2
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7472	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3749	Approved
0.7468	Intermediate Similarity	NPD2354	Approved
0.7468	Intermediate Similarity	NPD3887	Approved
0.7467	Intermediate Similarity	NPD6832	Phase 2
0.7451	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6959	Discontinued
0.7438	Intermediate Similarity	NPD2534	Approved
0.7438	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2533	Approved
0.7438	Intermediate Similarity	NPD3146	Approved
0.7438	Intermediate Similarity	NPD2532	Approved
0.7421	Intermediate Similarity	NPD7440	Discontinued
0.7419	Intermediate Similarity	NPD4308	Phase 3
0.7419	Intermediate Similarity	NPD3748	Approved
0.7417	Intermediate Similarity	NPD7095	Approved
0.7415	Intermediate Similarity	NPD1481	Phase 2
0.7405	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8166	Discontinued
0.7403	Intermediate Similarity	NPD6653	Approved
0.7403	Intermediate Similarity	NPD1607	Approved
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7386	Intermediate Similarity	NPD4060	Phase 1
0.7383	Intermediate Similarity	NPD2797	Approved
0.7379	Intermediate Similarity	NPD9268	Approved
0.7368	Intermediate Similarity	NPD3268	Approved
0.7362	Intermediate Similarity	NPD7458	Discontinued
0.7353	Intermediate Similarity	NPD3926	Phase 2
0.7347	Intermediate Similarity	NPD1535	Discovery
0.7342	Intermediate Similarity	NPD1652	Phase 2
0.7338	Intermediate Similarity	NPD4340	Discontinued
0.7337	Intermediate Similarity	NPD1247	Approved
0.7325	Intermediate Similarity	NPD2344	Approved
0.7315	Intermediate Similarity	NPD3225	Approved
0.731	Intermediate Similarity	NPD1894	Discontinued
0.7305	Intermediate Similarity	NPD228	Approved
0.7301	Intermediate Similarity	NPD3686	Approved
0.7301	Intermediate Similarity	NPD3687	Approved
0.7297	Intermediate Similarity	NPD9717	Approved
0.7289	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2861	Phase 2
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7240	Approved
0.7247	Intermediate Similarity	NPD8150	Discontinued
0.7244	Intermediate Similarity	NPD7097	Phase 1
0.7239	Intermediate Similarity	NPD920	Approved
0.723	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6844	Discontinued
0.7225	Intermediate Similarity	NPD2163	Approved
0.7219	Intermediate Similarity	NPD5647	Approved
0.7215	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2353	Approved
0.7211	Intermediate Similarity	NPD1778	Approved
0.7203	Intermediate Similarity	NPD1241	Discontinued
0.72	Intermediate Similarity	NPD5953	Discontinued
0.7184	Intermediate Similarity	NPD7286	Phase 2
0.7181	Intermediate Similarity	NPD3972	Approved
0.717	Intermediate Similarity	NPD2424	Discontinued
0.717	Intermediate Similarity	NPD4534	Discontinued
0.7167	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3496	Discontinued
0.7161	Intermediate Similarity	NPD1558	Phase 1
0.7161	Intermediate Similarity	NPD4307	Phase 2
0.716	Intermediate Similarity	NPD6971	Discontinued
0.716	Intermediate Similarity	NPD4357	Discontinued
0.7152	Intermediate Similarity	NPD2438	Suspended
0.7152	Intermediate Similarity	NPD824	Approved
0.7152	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD6099	Approved
0.7152	Intermediate Similarity	NPD6032	Approved
0.7143	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD5585	Approved
0.7134	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4536	Approved
0.7134	Intermediate Similarity	NPD4538	Approved
0.7126	Intermediate Similarity	NPD7177	Discontinued
0.7125	Intermediate Similarity	NPD6674	Discontinued
0.7125	Intermediate Similarity	NPD5698	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