NPASS Compound

Structure

NPC470130 OpenBabel07101718242D 31 34 0 0 1 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -5.1962 -0.0000 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 2.5981 -3.5000 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 0.8660 -4.5000 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 1.7321 -3.0000 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 -5.1962 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 10 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 14 1 0 0 0 0 5 10 2 0 0 0 0 5 15 1 0 0 0 0 6 11 2 0 0 0 0 6 19 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 9 20 1 0 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 31 1 0 0 0 0 19 21 2 0 0 0 0 19 31 1 0 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 22 29 2 0 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.08
Volume:	404.953
LogP:	2.102
LogD:	0.885
LogS:	-3.789
# Rotatable Bonds:	4
TPSA:	157.66
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	3.541
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.532
MDCK Permeability:	7.659376933588646e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.088
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.911
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	98.01461029052734%
Volume Distribution (VD):	0.321
Pgp-substrate:	2.1021814346313477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.482
CYP2C9-substrate:	0.677
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.266
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	9.905
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.557
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.303
Maximum Recommended Daily Dose:	0.41
Skin Sensitization:	0.923
Carcinogencity:	0.286
Eye Corrosion:	0.003
Eye Irritation:	0.641
Respiratory Toxicity:	0.075

Download Data

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

Natural Product: NPC470130

Natural Product ID:	NPC470130
*Common Name:**	Phellibaumin B
IUPAC Name:	2-[3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-8,9-dihydroxy-1-oxo-6H-pyrano[4,3-c]isochromen-6-yl]acetic acid
Synonyms:	Phellibaumin B
Standard InCHIKey:	ZWCIXZKNLVQESJ-HNQUOIGGSA-N
Standard InCHI:	InChI=1S/C22H16O9/c23-14-4-2-10(5-15(14)24)1-3-11-6-19-21(22(29)30-11)13-8-17(26)16(25)7-12(13)18(31-19)9-20(27)28/h1-8,18,23-26H,9H2,(H,27,28)/b3-1+
SMILES:	C1=CC(=C(C=C1C=CC2=CC3=C(C4=CC(=C(C=C4C(O3)CC(=O)O)O)O)C(=O)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1780025
PubChem CID:	53248680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20708931]
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21531558]
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26077494]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	41400.0	nM	PMID[559565]

☑ 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 NPC470130 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	398
0.1-0.2	1669
0.2-0.3	3989
0.3-0.4	9092
0.4-0.5	9141
0.5-0.6	3676
0.6-0.7	5411
0.7-0.8	6250
0.8-0.85	2706
0.85-0.9	342
0.9-0.95	22
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.942	High Similarity	NPC191280
0.9178	High Similarity	NPC270268
0.9155	High Similarity	NPC183824
0.9149	High Similarity	NPC91546
0.9085	High Similarity	NPC285550
0.9078	High Similarity	NPC9218
0.9078	High Similarity	NPC290664
0.9058	High Similarity	NPC106406
0.8904	High Similarity	NPC155910
0.8904	High Similarity	NPC17042
0.8873	High Similarity	NPC134969
0.8828	High Similarity	NPC257025
0.8776	High Similarity	NPC476463
0.8776	High Similarity	NPC1580
0.8733	High Similarity	NPC295646
0.8707	High Similarity	NPC229264
0.8662	High Similarity	NPC156307
0.8649	High Similarity	NPC471076
0.8649	High Similarity	NPC192568
0.8633	High Similarity	NPC285361
0.8623	High Similarity	NPC167463
0.8603	High Similarity	NPC85565
0.8601	High Similarity	NPC308976
0.8571	High Similarity	NPC318799
0.8562	High Similarity	NPC227062
0.8561	High Similarity	NPC64111
0.8561	High Similarity	NPC208536
0.8552	High Similarity	NPC38473
0.8543	High Similarity	NPC267091
0.8533	High Similarity	NPC32197
0.8533	High Similarity	NPC259576
0.8533	High Similarity	NPC221091
0.8526	High Similarity	NPC144557
0.8523	High Similarity	NPC472969
0.8521	High Similarity	NPC248150
0.8511	High Similarity	NPC18074
0.8511	High Similarity	NPC61
0.8511	High Similarity	NPC25581
0.8511	High Similarity	NPC5419
0.8506	High Similarity	NPC187205
0.8503	High Similarity	NPC226738
0.8503	High Similarity	NPC22176
0.8503	High Similarity	NPC190587
0.8503	High Similarity	NPC121573
0.8493	Intermediate Similarity	NPC13818
0.8493	Intermediate Similarity	NPC224389
0.8493	Intermediate Similarity	NPC297517
0.8493	Intermediate Similarity	NPC35702
0.8493	Intermediate Similarity	NPC477335
0.8493	Intermediate Similarity	NPC471027
0.8493	Intermediate Similarity	NPC206095
0.8489	Intermediate Similarity	NPC46192
0.8483	Intermediate Similarity	NPC156709
0.8483	Intermediate Similarity	NPC179505
0.8477	Intermediate Similarity	NPC243891
0.8477	Intermediate Similarity	NPC300329
0.8472	Intermediate Similarity	NPC100558
0.8472	Intermediate Similarity	NPC301915
0.8472	Intermediate Similarity	NPC261292
0.8472	Intermediate Similarity	NPC310252
0.8472	Intermediate Similarity	NPC84789
0.8472	Intermediate Similarity	NPC302583
0.8471	Intermediate Similarity	NPC223006
0.8471	Intermediate Similarity	NPC134047
0.8471	Intermediate Similarity	NPC272750
0.8471	Intermediate Similarity	NPC173729
0.8467	Intermediate Similarity	NPC476394
0.8467	Intermediate Similarity	NPC98809
0.8456	Intermediate Similarity	NPC322660
0.8451	Intermediate Similarity	NPC155209
0.8451	Intermediate Similarity	NPC168799
0.8446	Intermediate Similarity	NPC477333
0.8442	Intermediate Similarity	NPC153512
0.844	Intermediate Similarity	NPC198388
0.8435	Intermediate Similarity	NPC220664
0.8435	Intermediate Similarity	NPC43158
0.8435	Intermediate Similarity	NPC472016
0.8435	Intermediate Similarity	NPC277315
0.8435	Intermediate Similarity	NPC37331
0.8435	Intermediate Similarity	NPC258469
0.8435	Intermediate Similarity	NPC319628
0.8435	Intermediate Similarity	NPC303090
0.8435	Intermediate Similarity	NPC284948
0.8435	Intermediate Similarity	NPC192831
0.8431	Intermediate Similarity	NPC469888
0.8429	Intermediate Similarity	NPC94810
0.8428	Intermediate Similarity	NPC298847
0.8414	Intermediate Similarity	NPC152942
0.8414	Intermediate Similarity	NPC302857
0.8414	Intermediate Similarity	NPC142703
0.8414	Intermediate Similarity	NPC219428
0.8414	Intermediate Similarity	NPC37250
0.8414	Intermediate Similarity	NPC278068
0.8414	Intermediate Similarity	NPC257173
0.84	Intermediate Similarity	NPC142528
0.8397	Intermediate Similarity	NPC24627
0.8382	Intermediate Similarity	NPC472271
0.8377	Intermediate Similarity	NPC203757
0.8377	Intermediate Similarity	NPC67396
0.8375	Intermediate Similarity	NPC186100
0.8375	Intermediate Similarity	NPC216403
0.8375	Intermediate Similarity	NPC41494
0.8367	Intermediate Similarity	NPC158634
0.8356	Intermediate Similarity	NPC205751
0.8356	Intermediate Similarity	NPC474875
0.8356	Intermediate Similarity	NPC289690
0.8356	Intermediate Similarity	NPC26241
0.8356	Intermediate Similarity	NPC476820
0.8356	Intermediate Similarity	NPC274891
0.8356	Intermediate Similarity	NPC288452
0.8356	Intermediate Similarity	NPC476819
0.8356	Intermediate Similarity	NPC303683
0.8356	Intermediate Similarity	NPC295492
0.8355	Intermediate Similarity	NPC140151
0.8355	Intermediate Similarity	NPC85131
0.8345	Intermediate Similarity	NPC62907
0.8345	Intermediate Similarity	NPC67349
0.8345	Intermediate Similarity	NPC279676
0.8344	Intermediate Similarity	NPC42464
0.8333	Intermediate Similarity	NPC123988
0.8333	Intermediate Similarity	NPC315157
0.8333	Intermediate Similarity	NPC288945
0.8333	Intermediate Similarity	NPC221383
0.8333	Intermediate Similarity	NPC311742
0.8333	Intermediate Similarity	NPC299090
0.8333	Intermediate Similarity	NPC143892
0.8333	Intermediate Similarity	NPC283081
0.8323	Intermediate Similarity	NPC123208
0.8323	Intermediate Similarity	NPC24640
0.8323	Intermediate Similarity	NPC54928
0.8322	Intermediate Similarity	NPC223185
0.8312	Intermediate Similarity	NPC281703
0.8312	Intermediate Similarity	NPC125487
0.8312	Intermediate Similarity	NPC477299
0.8312	Intermediate Similarity	NPC137301
0.8302	Intermediate Similarity	NPC191930
0.8301	Intermediate Similarity	NPC204350
0.8301	Intermediate Similarity	NPC75695
0.8299	Intermediate Similarity	NPC155205
0.8299	Intermediate Similarity	NPC158472
0.8298	Intermediate Similarity	NPC226855
0.8291	Intermediate Similarity	NPC22324
0.8291	Intermediate Similarity	NPC322982
0.8291	Intermediate Similarity	NPC145847
0.8289	Intermediate Similarity	NPC306343
0.828	Intermediate Similarity	NPC328093
0.8278	Intermediate Similarity	NPC120621
0.8278	Intermediate Similarity	NPC43123
0.8278	Intermediate Similarity	NPC248257
0.8278	Intermediate Similarity	NPC473138
0.8278	Intermediate Similarity	NPC28776
0.8276	Intermediate Similarity	NPC156892
0.8269	Intermediate Similarity	NPC289322
0.8269	Intermediate Similarity	NPC475663
0.8269	Intermediate Similarity	NPC286919
0.8269	Intermediate Similarity	NPC114179
0.8269	Intermediate Similarity	NPC160512
0.8269	Intermediate Similarity	NPC68324
0.8269	Intermediate Similarity	NPC38779
0.8269	Intermediate Similarity	NPC156818
0.8267	Intermediate Similarity	NPC84786
0.8267	Intermediate Similarity	NPC98356
0.8264	Intermediate Similarity	NPC135127
0.8264	Intermediate Similarity	NPC474895
0.8258	Intermediate Similarity	NPC80534
0.8258	Intermediate Similarity	NPC16286
0.8258	Intermediate Similarity	NPC472890
0.8258	Intermediate Similarity	NPC82592
0.8258	Intermediate Similarity	NPC56786
0.8258	Intermediate Similarity	NPC478230
0.8258	Intermediate Similarity	NPC69043
0.8258	Intermediate Similarity	NPC16082
0.8255	Intermediate Similarity	NPC473090
0.8255	Intermediate Similarity	NPC474692
0.8255	Intermediate Similarity	NPC160378
0.8248	Intermediate Similarity	NPC147654
0.8247	Intermediate Similarity	NPC44730
0.8247	Intermediate Similarity	NPC115249
0.8247	Intermediate Similarity	NPC157898
0.8247	Intermediate Similarity	NPC478224
0.8247	Intermediate Similarity	NPC76041
0.8247	Intermediate Similarity	NPC184284
0.8243	Intermediate Similarity	NPC130485
0.8239	Intermediate Similarity	NPC109990
0.8239	Intermediate Similarity	NPC249181
0.8239	Intermediate Similarity	NPC186686
0.8235	Intermediate Similarity	NPC252979
0.8235	Intermediate Similarity	NPC472891
0.8231	Intermediate Similarity	NPC75763
0.8231	Intermediate Similarity	NPC474784
0.8231	Intermediate Similarity	NPC471819
0.8231	Intermediate Similarity	NPC225036
0.8231	Intermediate Similarity	NPC247409
0.8231	Intermediate Similarity	NPC32360
0.8231	Intermediate Similarity	NPC105525
0.8231	Intermediate Similarity	NPC12218
0.8228	Intermediate Similarity	NPC112418
0.8224	Intermediate Similarity	NPC119059
0.8224	Intermediate Similarity	NPC92117
0.8219	Intermediate Similarity	NPC78363

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 NPC470130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	925
0.2-0.3	1756
0.3-0.4	2581
0.4-0.5	1868
0.5-0.6	1036
0.6-0.7	441
0.7-0.8	123
0.8-0.85	44
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8435	Intermediate Similarity	NPD6190	Approved
0.8205	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1511	Approved
0.8077	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD230	Phase 1
0.8041	Intermediate Similarity	NPD7266	Discontinued
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.8013	Intermediate Similarity	NPD1934	Approved
0.7974	Intermediate Similarity	NPD1512	Approved
0.7962	Intermediate Similarity	NPD2801	Approved
0.7952	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6232	Discontinued
0.7927	Intermediate Similarity	NPD7054	Approved
0.7885	Intermediate Similarity	NPD4380	Phase 2
0.7879	Intermediate Similarity	NPD7472	Approved
0.7867	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD3818	Discontinued
0.7853	Intermediate Similarity	NPD6166	Phase 2
0.7853	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1465	Phase 2
0.7843	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6797	Phase 2
0.7805	Intermediate Similarity	NPD7473	Discontinued
0.7784	Intermediate Similarity	NPD7685	Pre-registration
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.7771	Intermediate Similarity	NPD7074	Phase 3
0.7764	Intermediate Similarity	NPD6234	Discontinued
0.7763	Intermediate Similarity	NPD4628	Phase 3
0.7763	Intermediate Similarity	NPD8166	Discontinued
0.774	Intermediate Similarity	NPD3764	Approved
0.7736	Intermediate Similarity	NPD7819	Suspended
0.7711	Intermediate Similarity	NPD5844	Phase 1
0.7706	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5402	Approved
0.7674	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3750	Approved
0.764	Intermediate Similarity	NPD3882	Suspended
0.7633	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7075	Discontinued
0.758	Intermediate Similarity	NPD5403	Approved
0.7571	Intermediate Similarity	NPD9545	Approved
0.7564	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD37	Approved
0.755	Intermediate Similarity	NPD1510	Phase 2
0.7545	Intermediate Similarity	NPD7228	Approved
0.7531	Intermediate Similarity	NPD4965	Approved
0.7531	Intermediate Similarity	NPD4966	Approved
0.7531	Intermediate Similarity	NPD4967	Phase 2
0.7517	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7455	Intermediate Similarity	NPD7199	Phase 2
0.7455	Intermediate Similarity	NPD6959	Discontinued
0.7453	Intermediate Similarity	NPD6801	Discontinued
0.7452	Intermediate Similarity	NPD2533	Approved
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2534	Approved
0.7452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5401	Approved
0.7452	Intermediate Similarity	NPD2532	Approved
0.7451	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7033	Discontinued
0.7434	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3027	Phase 3
0.7431	Intermediate Similarity	NPD1608	Approved
0.7431	Intermediate Similarity	NPD9269	Phase 2
0.7407	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1549	Phase 2
0.7391	Intermediate Similarity	NPD7411	Suspended
0.7389	Intermediate Similarity	NPD6799	Approved
0.7386	Intermediate Similarity	NPD5406	Approved
0.7386	Intermediate Similarity	NPD5405	Approved
0.7386	Intermediate Similarity	NPD5404	Approved
0.7386	Intermediate Similarity	NPD5408	Approved
0.7383	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3455	Phase 2
0.7375	Intermediate Similarity	NPD3226	Approved
0.7365	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8150	Discontinued
0.7355	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7333	Intermediate Similarity	NPD6233	Phase 2
0.7329	Intermediate Similarity	NPD3225	Approved
0.732	Intermediate Similarity	NPD3748	Approved
0.7312	Intermediate Similarity	NPD1653	Approved
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7297	Intermediate Similarity	NPD9494	Approved
0.7294	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5494	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1613	Approved
0.7285	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD2438	Suspended
0.7273	Intermediate Similarity	NPD2796	Approved
0.7273	Intermediate Similarity	NPD3749	Approved
0.7246	Intermediate Similarity	NPD8127	Discontinued
0.7233	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD17	Approved
0.7222	Intermediate Similarity	NPD6599	Discontinued
0.7219	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7768	Phase 2
0.7211	Intermediate Similarity	NPD1283	Approved
0.7195	Intermediate Similarity	NPD8455	Phase 2
0.7188	Intermediate Similarity	NPD6273	Approved
0.7178	Intermediate Similarity	NPD6386	Approved
0.7178	Intermediate Similarity	NPD6385	Approved
0.7171	Intermediate Similarity	NPD2979	Phase 3
0.7171	Intermediate Similarity	NPD4060	Phase 1
0.7171	Intermediate Similarity	NPD1240	Approved
0.717	Intermediate Similarity	NPD7390	Discontinued
0.7162	Intermediate Similarity	NPD2797	Approved
0.7161	Intermediate Similarity	NPD9570	Approved
0.7161	Intermediate Similarity	NPD1551	Phase 2
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD9268	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7152	Intermediate Similarity	NPD3268	Approved
0.7133	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD447	Suspended
0.7124	Intermediate Similarity	NPD6355	Discontinued
0.7123	Intermediate Similarity	NPD1201	Approved
0.7115	Intermediate Similarity	NPD2346	Discontinued
0.7105	Intermediate Similarity	NPD6663	Approved
0.7089	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4110	Phase 3
0.7078	Intermediate Similarity	NPD1607	Approved
0.7075	Intermediate Similarity	NPD1481	Phase 2
0.7069	Intermediate Similarity	NPD7240	Approved
0.7069	Intermediate Similarity	NPD6559	Discontinued
0.7067	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5736	Approved
0.7062	Intermediate Similarity	NPD8434	Phase 2
0.705	Intermediate Similarity	NPD3021	Approved
0.705	Intermediate Similarity	NPD3022	Approved
0.7047	Intermediate Similarity	NPD1203	Approved
0.7047	Intermediate Similarity	NPD1470	Approved
0.7039	Intermediate Similarity	NPD2313	Discontinued
0.702	Intermediate Similarity	NPD6832	Phase 2
0.7013	Intermediate Similarity	NPD4340	Discontinued
0.7007	Intermediate Similarity	NPD1535	Discovery
0.7007	Intermediate Similarity	NPD1281	Approved
0.6993	Remote Similarity	NPD4062	Phase 3
0.6987	Remote Similarity	NPD2799	Discontinued
0.6987	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7003	Approved
0.6981	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7095	Approved
0.6966	Remote Similarity	NPD1894	Discontinued
0.6959	Remote Similarity	NPD5242	Approved
0.6954	Remote Similarity	NPD2861	Phase 2
0.6951	Remote Similarity	NPD7458	Discontinued
0.6948	Remote Similarity	NPD825	Approved
0.6948	Remote Similarity	NPD826	Approved
0.6944	Remote Similarity	NPD9493	Approved
0.6923	Remote Similarity	NPD919	Approved
0.6914	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1933	Approved
0.6903	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7229	Phase 3
0.6901	Remote Similarity	NPD5710	Approved
0.6901	Remote Similarity	NPD5711	Approved
0.6898	Remote Similarity	NPD7435	Discontinued
0.6897	Remote Similarity	NPD5536	Phase 2
0.6894	Remote Similarity	NPD3300	Phase 2
0.6892	Remote Similarity	NPD3705	Approved
0.6887	Remote Similarity	NPD2798	Approved
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3400	Discontinued
0.6875	Remote Similarity	NPD7038	Approved
0.6875	Remote Similarity	NPD7039	Approved
0.6871	Remote Similarity	NPD4626	Approved
0.6859	Remote Similarity	NPD6653	Approved
0.6854	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4288	Approved
0.6845	Remote Similarity	NPD5353	Approved
0.6839	Remote Similarity	NPD3620	Phase 2
0.6839	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7177	Discontinued
0.6835	Remote Similarity	NPD6100	Approved
0.6835	Remote Similarity	NPD6099	Approved
0.6835	Remote Similarity	NPD4477	Approved
0.6835	Remote Similarity	NPD4476	Approved
0.6835	Remote Similarity	NPD2531	Phase 2
0.6831	Remote Similarity	NPD6535	Approved
0.6831	Remote Similarity	NPD228	Approved
0.6831	Remote Similarity	NPD6534	Approved
0.6828	Remote Similarity	NPD6782	Approved
0.6828	Remote Similarity	NPD6778	Approved
0.6828	Remote Similarity	NPD6781	Approved
0.6828	Remote Similarity	NPD6777	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data