NPASS Compound

Structure

NPC290695 OpenBabel07101719252D 27 31 0 0 1 0 0 0 0 0999 V2000 4.4231 -0.6203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4343 -0.7693 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 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -2.6361 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 1.3639 0.5353 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 -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 2 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 1.9890 -1.8271 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 0.5531 0.5961 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8220 -0.1365 0.0000 C 0 0 1 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 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.9135 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 -4.4152 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 -1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1877 1.5269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8108 0.0125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 27 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 13 2 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 20 2 0 0 0 0 11 18 1 0 0 0 0 11 19 2 0 0 0 0 12 8 1 1 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 21 2 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 25 2 0 0 0 0 16 22 1 0 0 0 0 16 26 1 1 0 0 0 17 21 1 0 0 0 0 17 27 1 6 0 0 0 18 22 2 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.13
Volume:	369.145
LogP:	4.73
LogD:	2.401
LogS:	-5.332
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.847
Synthetic Accessibility Score:	3.976
Fsp3:	0.364
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:	-5.015
MDCK Permeability:	1.8290722437086515e-05
Pgp-inhibitor:	0.323
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.304
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	94.98743438720703%
Volume Distribution (VD):	1.18
Pgp-substrate:	2.3784611225128174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.133
CYP1A2-substrate:	0.862
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.57
CYP2C9-inhibitor:	0.716
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.275
CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.478

ADMET: Excretion

Clearance (CL):	3.062
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.207
Human Hepatotoxicity (H-HT):	0.86
Drug-inuced Liver Injury (DILI):	0.759
AMES Toxicity:	0.811
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.649
Carcinogencity:	0.103
Eye Corrosion:	0.003
Eye Irritation:	0.291
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC290695

Natural Product ID:	NPC290695
*Common Name:**	Hypoxylonol A
IUPAC Name:	n.a.
Synonyms:	Hypoxylonol A
Standard InCHIKey:	DSVFBOXMAJTYHV-DQYPLSBCSA-N
Standard InCHI:	InChI=1S/C22H20O5/c1-2-27-17-9-16(26)22-18-11-4-3-5-13(23)19(11)15(25)8-12(18)10-6-7-14(24)21(17)20(10)22/h3-7,12,16-17,23-24,26H,2,8-9H2,1H3/t12-,16+,17+/m1/s1
SMILES:	CCO[C@H]1C[C@@H](C2=C3c4cccc(c4C(=O)C[C@@H]3c3ccc(c1c23)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1950966
PubChem CID:	57333713
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO30840	Hypoxylon truncatum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253861]
NPO30840	Hypoxylon truncatum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21082806]
NPO30840	Hypoxylon truncatum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148396]

☑ 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
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	15000.0	nM	PMID[453349]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16000.0	nM	PMID[453349]

☑ 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 NPC290695 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	339
0.1-0.2	1290
0.2-0.3	2589
0.3-0.4	6438
0.4-0.5	12107
0.5-0.6	4297
0.6-0.7	6354
0.7-0.8	7356
0.8-0.85	1651
0.85-0.9	267
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC106524
0.9929	High Similarity	NPC162751
0.9929	High Similarity	NPC52161
0.9504	High Similarity	NPC91019
0.9504	High Similarity	NPC106519
0.9128	High Similarity	NPC477276
0.8816	High Similarity	NPC478220
0.8792	High Similarity	NPC470570
0.8725	High Similarity	NPC34482
0.8662	High Similarity	NPC18380
0.8658	High Similarity	NPC21599
0.8658	High Similarity	NPC48762
0.8658	High Similarity	NPC193703
0.8654	High Similarity	NPC186113
0.8654	High Similarity	NPC195167
0.8636	High Similarity	NPC478218
0.8627	High Similarity	NPC470569
0.8618	High Similarity	NPC329933
0.8608	High Similarity	NPC478229
0.86	High Similarity	NPC170055
0.8599	High Similarity	NPC184326
0.8599	High Similarity	NPC292863
0.8591	High Similarity	NPC471731
0.8571	High Similarity	NPC87708
0.8571	High Similarity	NPC474534
0.8571	High Similarity	NPC474533
0.8562	High Similarity	NPC470568
0.8562	High Similarity	NPC477914
0.8562	High Similarity	NPC290954
0.8562	High Similarity	NPC255641
0.8562	High Similarity	NPC205766
0.8553	High Similarity	NPC290160
0.8544	High Similarity	NPC137232
0.8544	High Similarity	NPC478222
0.8543	High Similarity	NPC147250
0.8535	High Similarity	NPC472617
0.8535	High Similarity	NPC324736
0.8533	High Similarity	NPC477913
0.8533	High Similarity	NPC42540
0.8533	High Similarity	NPC218866
0.8533	High Similarity	NPC151607
0.8533	High Similarity	NPC48130
0.8533	High Similarity	NPC84568
0.8533	High Similarity	NPC300684
0.8523	High Similarity	NPC474961
0.8523	High Similarity	NPC471733
0.8523	High Similarity	NPC135524
0.8523	High Similarity	NPC85310
0.8516	High Similarity	NPC135522
0.8516	High Similarity	NPC182921
0.8516	High Similarity	NPC218870
0.8516	High Similarity	NPC329844
0.8516	High Similarity	NPC474824
0.8516	High Similarity	NPC470408
0.8514	High Similarity	NPC168471
0.8506	High Similarity	NPC476553
0.8506	High Similarity	NPC476552
0.8506	High Similarity	NPC474417
0.8506	High Similarity	NPC478148
0.8506	High Similarity	NPC149526
0.8506	High Similarity	NPC476551
0.8506	High Similarity	NPC232645
0.8506	High Similarity	NPC72958
0.8497	Intermediate Similarity	NPC477221
0.8497	Intermediate Similarity	NPC478219
0.8491	Intermediate Similarity	NPC473961
0.8487	Intermediate Similarity	NPC119767
0.8487	Intermediate Similarity	NPC34802
0.8481	Intermediate Similarity	NPC284495
0.8481	Intermediate Similarity	NPC472618
0.8477	Intermediate Similarity	NPC478019
0.8467	Intermediate Similarity	NPC159721
0.8467	Intermediate Similarity	NPC313047
0.8467	Intermediate Similarity	NPC3732
0.8467	Intermediate Similarity	NPC295712
0.8467	Intermediate Similarity	NPC451542
0.8467	Intermediate Similarity	NPC474203
0.8462	Intermediate Similarity	NPC66508
0.8462	Intermediate Similarity	NPC226656
0.8456	Intermediate Similarity	NPC472604
0.8456	Intermediate Similarity	NPC305845
0.8456	Intermediate Similarity	NPC204045
0.8456	Intermediate Similarity	NPC472603
0.8456	Intermediate Similarity	NPC477275
0.8456	Intermediate Similarity	NPC472605
0.8452	Intermediate Similarity	NPC470337
0.8452	Intermediate Similarity	NPC113608
0.8452	Intermediate Similarity	NPC470338
0.8452	Intermediate Similarity	NPC51824
0.8452	Intermediate Similarity	NPC154683
0.8452	Intermediate Similarity	NPC43345
0.8452	Intermediate Similarity	NPC268992
0.8452	Intermediate Similarity	NPC40356
0.8442	Intermediate Similarity	NPC147735
0.8435	Intermediate Similarity	NPC301915
0.8435	Intermediate Similarity	NPC261292
0.8431	Intermediate Similarity	NPC221352
0.8431	Intermediate Similarity	NPC35150
0.8431	Intermediate Similarity	NPC106328
0.8428	Intermediate Similarity	NPC312273
0.8428	Intermediate Similarity	NPC301256
0.8421	Intermediate Similarity	NPC285122
0.8421	Intermediate Similarity	NPC472134
0.8414	Intermediate Similarity	NPC314048
0.8408	Intermediate Similarity	NPC474861
0.8408	Intermediate Similarity	NPC478223
0.8403	Intermediate Similarity	NPC72669
0.8403	Intermediate Similarity	NPC474517
0.84	Intermediate Similarity	NPC232021
0.84	Intermediate Similarity	NPC126534
0.84	Intermediate Similarity	NPC40118
0.84	Intermediate Similarity	NPC469520
0.8397	Intermediate Similarity	NPC210942
0.8397	Intermediate Similarity	NPC169990
0.8397	Intermediate Similarity	NPC470102
0.8397	Intermediate Similarity	NPC474622
0.8397	Intermediate Similarity	NPC474621
0.8389	Intermediate Similarity	NPC472601
0.8389	Intermediate Similarity	NPC155205
0.8389	Intermediate Similarity	NPC181560
0.8389	Intermediate Similarity	NPC169452
0.8389	Intermediate Similarity	NPC472600
0.8387	Intermediate Similarity	NPC258249
0.8387	Intermediate Similarity	NPC178484
0.8385	Intermediate Similarity	NPC478022
0.8385	Intermediate Similarity	NPC469664
0.8385	Intermediate Similarity	NPC478020
0.8378	Intermediate Similarity	NPC94248
0.8378	Intermediate Similarity	NPC478200
0.8378	Intermediate Similarity	NPC212693
0.8378	Intermediate Similarity	NPC191835
0.8378	Intermediate Similarity	NPC33144
0.8377	Intermediate Similarity	NPC97028
0.8377	Intermediate Similarity	NPC100985
0.8377	Intermediate Similarity	NPC158338
0.8377	Intermediate Similarity	NPC97029
0.8377	Intermediate Similarity	NPC473016
0.8377	Intermediate Similarity	NPC288036
0.8377	Intermediate Similarity	NPC65589
0.8375	Intermediate Similarity	NPC473012
0.8375	Intermediate Similarity	NPC15374
0.8375	Intermediate Similarity	NPC315772
0.8367	Intermediate Similarity	NPC291454
0.8367	Intermediate Similarity	NPC191976
0.8366	Intermediate Similarity	NPC71055
0.8366	Intermediate Similarity	NPC312929
0.8366	Intermediate Similarity	NPC289042
0.8366	Intermediate Similarity	NPC56433
0.8366	Intermediate Similarity	NPC215593
0.8366	Intermediate Similarity	NPC118027
0.8366	Intermediate Similarity	NPC190648
0.8366	Intermediate Similarity	NPC472135
0.8366	Intermediate Similarity	NPC261271
0.8366	Intermediate Similarity	NPC245584
0.8366	Intermediate Similarity	NPC290194
0.8366	Intermediate Similarity	NPC475348
0.8366	Intermediate Similarity	NPC126767
0.8366	Intermediate Similarity	NPC471734
0.8365	Intermediate Similarity	NPC470810
0.8356	Intermediate Similarity	NPC161964
0.8356	Intermediate Similarity	NPC472262
0.8356	Intermediate Similarity	NPC287604
0.8355	Intermediate Similarity	NPC271288
0.8354	Intermediate Similarity	NPC272196
0.8354	Intermediate Similarity	NPC208258
0.8354	Intermediate Similarity	NPC257166
0.8354	Intermediate Similarity	NPC475184
0.8345	Intermediate Similarity	NPC165612
0.8344	Intermediate Similarity	NPC478133
0.8344	Intermediate Similarity	NPC293545
0.8344	Intermediate Similarity	NPC84266
0.8344	Intermediate Similarity	NPC37253
0.8344	Intermediate Similarity	NPC297600
0.8344	Intermediate Similarity	NPC300307
0.8344	Intermediate Similarity	NPC192219
0.8344	Intermediate Similarity	NPC174905
0.8344	Intermediate Similarity	NPC174599
0.8344	Intermediate Similarity	NPC476473
0.8344	Intermediate Similarity	NPC478202
0.8344	Intermediate Similarity	NPC82190
0.8344	Intermediate Similarity	NPC68727
0.8344	Intermediate Similarity	NPC79375
0.8344	Intermediate Similarity	NPC66029
0.8333	Intermediate Similarity	NPC313123
0.8333	Intermediate Similarity	NPC474843
0.8333	Intermediate Similarity	NPC130485
0.8333	Intermediate Similarity	NPC478217
0.8333	Intermediate Similarity	NPC470340
0.8333	Intermediate Similarity	NPC265178
0.8333	Intermediate Similarity	NPC53649
0.8333	Intermediate Similarity	NPC158634
0.8333	Intermediate Similarity	NPC180944
0.8323	Intermediate Similarity	NPC473009
0.8323	Intermediate Similarity	NPC37348
0.8323	Intermediate Similarity	NPC476505
0.8323	Intermediate Similarity	NPC472633
0.8323	Intermediate Similarity	NPC476295
0.8323	Intermediate Similarity	NPC202595
0.8322	Intermediate Similarity	NPC242994
0.8322	Intermediate Similarity	NPC88269

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 NPC290695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	850
0.2-0.3	1392
0.3-0.4	2468
0.4-0.5	2237
0.5-0.6	1179
0.6-0.7	536
0.7-0.8	167
0.8-0.85	22
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8313	Intermediate Similarity	NPD6959	Discontinued
0.8228	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD5408	Approved
0.8188	Intermediate Similarity	NPD5404	Approved
0.8188	Intermediate Similarity	NPD5405	Approved
0.8188	Intermediate Similarity	NPD5406	Approved
0.817	Intermediate Similarity	NPD7390	Discontinued
0.8121	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD4380	Phase 2
0.8085	Intermediate Similarity	NPD1201	Approved
0.805	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1470	Approved
0.795	Intermediate Similarity	NPD7768	Phase 2
0.7895	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7473	Discontinued
0.7885	Intermediate Similarity	NPD2532	Approved
0.7885	Intermediate Similarity	NPD2534	Approved
0.7885	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2533	Approved
0.7881	Intermediate Similarity	NPD1510	Phase 2
0.7843	Intermediate Similarity	NPD1549	Phase 2
0.7843	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6273	Approved
0.7829	Intermediate Similarity	NPD2935	Discontinued
0.7818	Intermediate Similarity	NPD6232	Discontinued
0.7812	Intermediate Similarity	NPD7411	Suspended
0.7799	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1934	Approved
0.7748	Intermediate Similarity	NPD1607	Approved
0.7742	Intermediate Similarity	NPD3750	Approved
0.7733	Intermediate Similarity	NPD1240	Approved
0.7725	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6166	Phase 2
0.7718	Intermediate Similarity	NPD3764	Approved
0.7712	Intermediate Similarity	NPD2796	Approved
0.7697	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD5844	Phase 1
0.7688	Intermediate Similarity	NPD3226	Approved
0.7683	Intermediate Similarity	NPD7075	Discontinued
0.7674	Intermediate Similarity	NPD8312	Approved
0.7674	Intermediate Similarity	NPD8313	Approved
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6559	Discontinued
0.7644	Intermediate Similarity	NPD8150	Discontinued
0.7628	Intermediate Similarity	NPD7003	Approved
0.7607	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3749	Approved
0.7576	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3019	Approved
0.7564	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7547	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6801	Discontinued
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD2801	Approved
0.7486	Intermediate Similarity	NPD6534	Approved
0.7486	Intermediate Similarity	NPD6535	Approved
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2932	Approved
0.7442	Intermediate Similarity	NPD7074	Phase 3
0.7439	Intermediate Similarity	NPD37	Approved
0.7434	Intermediate Similarity	NPD6663	Approved
0.7427	Intermediate Similarity	NPD3818	Discontinued
0.7419	Intermediate Similarity	NPD3748	Approved
0.7414	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD4966	Approved
0.741	Intermediate Similarity	NPD4967	Phase 2
0.7405	Intermediate Similarity	NPD8166	Discontinued
0.74	Intermediate Similarity	NPD5736	Approved
0.7391	Intermediate Similarity	NPD1512	Approved
0.7386	Intermediate Similarity	NPD943	Approved
0.7384	Intermediate Similarity	NPD7054	Approved
0.7377	Intermediate Similarity	NPD6782	Approved
0.7377	Intermediate Similarity	NPD6776	Approved
0.7377	Intermediate Similarity	NPD6778	Approved
0.7377	Intermediate Similarity	NPD6779	Approved
0.7377	Intermediate Similarity	NPD6777	Approved
0.7377	Intermediate Similarity	NPD6781	Approved
0.7377	Intermediate Similarity	NPD6780	Approved
0.7372	Intermediate Similarity	NPD1551	Phase 2
0.7363	Intermediate Similarity	NPD7699	Phase 2
0.7363	Intermediate Similarity	NPD7700	Phase 2
0.7362	Intermediate Similarity	NPD7458	Discontinued
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7349	Intermediate Similarity	NPD5402	Approved
0.7346	Intermediate Similarity	NPD5403	Approved
0.7342	Intermediate Similarity	NPD2800	Approved
0.7341	Intermediate Similarity	NPD7472	Approved
0.7333	Intermediate Similarity	NPD2798	Approved
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.7317	Intermediate Similarity	NPD6599	Discontinued
0.7315	Intermediate Similarity	NPD1876	Approved
0.7312	Intermediate Similarity	NPD8320	Phase 1
0.7312	Intermediate Similarity	NPD8319	Approved
0.7305	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6797	Phase 2
0.7297	Intermediate Similarity	NPD6823	Phase 2
0.7296	Intermediate Similarity	NPD4628	Phase 3
0.7296	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5711	Approved
0.7294	Intermediate Similarity	NPD5710	Approved
0.729	Intermediate Similarity	NPD6651	Approved
0.7289	Intermediate Similarity	NPD5761	Phase 2
0.7289	Intermediate Similarity	NPD5760	Phase 2
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1164	Approved
0.7267	Intermediate Similarity	NPD6799	Approved
0.7261	Intermediate Similarity	NPD6100	Approved
0.7261	Intermediate Similarity	NPD6099	Approved
0.7258	Intermediate Similarity	NPD7698	Approved
0.7258	Intermediate Similarity	NPD7696	Phase 3
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7258	Intermediate Similarity	NPD7697	Approved
0.7257	Intermediate Similarity	NPD7251	Discontinued
0.7246	Intermediate Similarity	NPD3817	Phase 2
0.7238	Intermediate Similarity	NPD6213	Phase 3
0.7238	Intermediate Similarity	NPD6212	Phase 3
0.7238	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8127	Discontinued
0.7235	Intermediate Similarity	NPD7199	Phase 2
0.7225	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD5401	Approved
0.7219	Intermediate Similarity	NPD7870	Phase 2
0.7219	Intermediate Similarity	NPD7871	Phase 2
0.7216	Intermediate Similarity	NPD7808	Phase 3
0.7215	Intermediate Similarity	NPD2344	Approved
0.7205	Intermediate Similarity	NPD3300	Phase 2
0.7205	Intermediate Similarity	NPD7236	Approved
0.72	Intermediate Similarity	NPD1283	Approved
0.7197	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3091	Approved
0.719	Intermediate Similarity	NPD4625	Phase 3
0.7188	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD9493	Approved
0.7172	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2861	Phase 2
0.7162	Intermediate Similarity	NPD3023	Approved
0.7162	Intermediate Similarity	NPD3026	Approved
0.7152	Intermediate Similarity	NPD3094	Phase 2
0.7143	Intermediate Similarity	NPD3024	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3025	Approved
0.7143	Intermediate Similarity	NPD1651	Approved
0.7126	Intermediate Similarity	NPD7177	Discontinued
0.7119	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3092	Approved
0.7105	Intermediate Similarity	NPD7701	Phase 2
0.7104	Intermediate Similarity	NPD4363	Phase 3
0.7104	Intermediate Similarity	NPD4360	Phase 2
0.7102	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7229	Phase 3
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7089	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7033	Discontinued
0.7083	Intermediate Similarity	NPD7801	Approved
0.7078	Intermediate Similarity	NPD7008	Discontinued
0.7078	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD9545	Approved
0.7075	Intermediate Similarity	NPD7741	Discontinued
0.7068	Intermediate Similarity	NPD8151	Discontinued
0.7052	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2979	Phase 3
0.7051	Intermediate Similarity	NPD4060	Phase 1
0.7051	Intermediate Similarity	NPD4140	Approved
0.7044	Intermediate Similarity	NPD2438	Suspended
0.7039	Intermediate Similarity	NPD2797	Approved
0.7039	Intermediate Similarity	NPD1203	Approved
0.7037	Intermediate Similarity	NPD2309	Approved
0.7037	Intermediate Similarity	NPD6190	Approved
0.7032	Intermediate Similarity	NPD3268	Approved
0.7032	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7874	Approved
0.703	Intermediate Similarity	NPD920	Approved
0.7029	Intermediate Similarity	NPD3751	Discontinued
0.702	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1243	Approved
0.7019	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6832	Phase 2
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD230	Phase 1
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7006	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD6002	Phase 3
0.7	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD7211	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