NPASS Compound

Structure

NPC3036 OpenBabel07101719522D 22 24 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 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 1.7321 0.0000 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 -2.5981 0.5000 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 0.8660 1.5000 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 0.8660 0.5000 0.0000 C 0 0 2 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 4.3301 1.5000 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 -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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 1 2 2 0 0 0 0 1 8 1 0 0 0 0 2 11 1 0 0 0 0 3 8 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 22 1 0 0 0 0 9 3 1 1 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 16 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	2.176
LogD:	2.469
LogS:	-3.647
# Rotatable Bonds:	2
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	3.089
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.999
MDCK Permeability:	7.315234597626841e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.147
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	96.95404815673828%
Volume Distribution (VD):	0.474
Pgp-substrate:	2.833078384399414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.327
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.83
CYP2D6-inhibitor:	0.665
CYP2D6-substrate:	0.781
CYP3A4-inhibitor:	0.643
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	18.412
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.742
AMES Toxicity:	0.721
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.331
Skin Sensitization:	0.948
Carcinogencity:	0.538
Eye Corrosion:	0.003
Eye Irritation:	0.934
Respiratory Toxicity:	0.063

Download Data

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

Natural Product: NPC3036

Natural Product ID:	NPC3036
*Common Name:**	GVVKSKFIFOYDOK-SECBINFHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GVVKSKFIFOYDOK-SECBINFHSA-N
Standard InCHI:	InChI=1S/C16H14O6/c17-10-5-13(20)15-14(6-10)22-7-9(16(15)21)3-8-1-2-11(18)12(19)4-8/h1-2,4-6,9,17-20H,3,7H2/t9-/m1/s1
SMILES:	Oc1cc(O)c2c(c1)OC[C@H](C2=O)Cc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594090
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans [CHEMONTID:0002898] Homoisoflavanones

*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
NPO33045	bellevalia eigii	Species	Hyacinthaceae	Eukaryota	Bulbs	Irbid, Jordan	n.a.	PMID[26147490]
NPO40241	Hyacinthaceae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[30951308]

☑ 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	4
IC50	2

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	20000.0	nM	PMID[541447]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	20000.0	nM	PMID[541447]
NPT737	Cell Line	HUVEC	Homo sapiens	GI50	>	100000.0	nM	PMID[541448]
NPT5265	Cell Line	Y79	Homo sapiens	GI50	>	100000.0	nM	PMID[541448]
NPT2	Others	Unspecified		GI50	>	100000.0	nM	PMID[541448]

☑ 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 NPC3036 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	411
0.1-0.2	1671
0.2-0.3	4370
0.3-0.4	10938
0.4-0.5	6842
0.5-0.6	3464
0.6-0.7	4820
0.7-0.8	5727
0.8-0.85	2461
0.85-0.9	1628
0.9-0.95	325
0.95-1	40

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC105512
0.9789	High Similarity	NPC95864
0.9724	High Similarity	NPC260979
0.9724	High Similarity	NPC472912
0.972	High Similarity	NPC294852
0.972	High Similarity	NPC188679
0.972	High Similarity	NPC321011
0.9658	High Similarity	NPC469550
0.9653	High Similarity	NPC1612
0.9653	High Similarity	NPC183959
0.9589	High Similarity	NPC236637
0.9589	High Similarity	NPC302950
0.9589	High Similarity	NPC219582
0.9583	High Similarity	NPC119059
0.9524	High Similarity	NPC213896
0.9524	High Similarity	NPC141212
0.9524	High Similarity	NPC192083
0.9524	High Similarity	NPC18727
0.9521	High Similarity	NPC31363
0.9521	High Similarity	NPC204515
0.9514	High Similarity	NPC108406
0.9463	High Similarity	NPC245758
0.9463	High Similarity	NPC472911
0.9463	High Similarity	NPC472910
0.9463	High Similarity	NPC129684
0.9463	High Similarity	NPC472913
0.9463	High Similarity	NPC222814
0.9463	High Similarity	NPC96167
0.9463	High Similarity	NPC472914
0.9463	High Similarity	NPC299520
0.9459	High Similarity	NPC321779
0.9459	High Similarity	NPC67396
0.9456	High Similarity	NPC260491
0.9456	High Similarity	NPC477231
0.9456	High Similarity	NPC61506
0.9456	High Similarity	NPC106976
0.9456	High Similarity	NPC240476
0.9456	High Similarity	NPC9743
0.9456	High Similarity	NPC257648
0.9456	High Similarity	NPC36835
0.9456	High Similarity	NPC246162
0.9452	High Similarity	NPC29231
0.9452	High Similarity	NPC62042
0.9448	High Similarity	NPC43669
0.9448	High Similarity	NPC272721
0.9448	High Similarity	NPC196277
0.9448	High Similarity	NPC276930
0.9441	High Similarity	NPC279121
0.9441	High Similarity	NPC242893
0.9441	High Similarity	NPC38065
0.9396	High Similarity	NPC235165
0.9396	High Similarity	NPC291878
0.9396	High Similarity	NPC24640
0.9396	High Similarity	NPC474638
0.9396	High Similarity	NPC255106
0.9396	High Similarity	NPC278778
0.9396	High Similarity	NPC320825
0.9396	High Similarity	NPC326037
0.9396	High Similarity	NPC471500
0.9396	High Similarity	NPC13858
0.9396	High Similarity	NPC35038
0.9396	High Similarity	NPC195796
0.9392	High Similarity	NPC325028
0.9392	High Similarity	NPC246328
0.9392	High Similarity	NPC74924
0.9392	High Similarity	NPC27532
0.9392	High Similarity	NPC256346
0.9392	High Similarity	NPC298692
0.9384	High Similarity	NPC87125
0.9384	High Similarity	NPC52005
0.9384	High Similarity	NPC287101
0.9384	High Similarity	NPC183950
0.9384	High Similarity	NPC223579
0.9384	High Similarity	NPC270465
0.9384	High Similarity	NPC137062
0.9379	High Similarity	NPC77378
0.9375	High Similarity	NPC70136
0.9371	High Similarity	NPC175013
0.9362	High Similarity	NPC118813
0.9333	High Similarity	NPC471479
0.9333	High Similarity	NPC474208
0.9333	High Similarity	NPC291508
0.9333	High Similarity	NPC52530
0.9333	High Similarity	NPC474836
0.9333	High Similarity	NPC474055
0.9333	High Similarity	NPC471515
0.9333	High Similarity	NPC471209
0.9333	High Similarity	NPC469584
0.9333	High Similarity	NPC156057
0.9333	High Similarity	NPC27337
0.9333	High Similarity	NPC99597
0.9333	High Similarity	NPC162869
0.9333	High Similarity	NPC67876
0.9333	High Similarity	NPC48208
0.9333	High Similarity	NPC472598
0.9333	High Similarity	NPC210084
0.9333	High Similarity	NPC475267
0.9329	High Similarity	NPC2928
0.9329	High Similarity	NPC152951
0.9329	High Similarity	NPC230149
0.9329	High Similarity	NPC57674
0.9329	High Similarity	NPC477503
0.9329	High Similarity	NPC45849
0.9329	High Similarity	NPC31018
0.9329	High Similarity	NPC168247
0.9329	High Similarity	NPC472909
0.9329	High Similarity	NPC470327
0.9329	High Similarity	NPC255807
0.9329	High Similarity	NPC117992
0.9329	High Similarity	NPC200761
0.9324	High Similarity	NPC120537
0.9324	High Similarity	NPC19721
0.9324	High Similarity	NPC199100
0.9324	High Similarity	NPC180234
0.932	High Similarity	NPC149127
0.932	High Similarity	NPC286342
0.932	High Similarity	NPC184136
0.932	High Similarity	NPC188871
0.932	High Similarity	NPC338131
0.932	High Similarity	NPC3825
0.932	High Similarity	NPC88804
0.932	High Similarity	NPC61620
0.9315	High Similarity	NPC120464
0.9315	High Similarity	NPC203747
0.9315	High Similarity	NPC194653
0.9315	High Similarity	NPC139364
0.9315	High Similarity	NPC80710
0.9315	High Similarity	NPC194856
0.9315	High Similarity	NPC254702
0.931	High Similarity	NPC20791
0.931	High Similarity	NPC179271
0.9301	High Similarity	NPC284556
0.9301	High Similarity	NPC301178
0.9296	High Similarity	NPC261234
0.9296	High Similarity	NPC316480
0.9276	High Similarity	NPC266314
0.9272	High Similarity	NPC53545
0.9272	High Similarity	NPC117418
0.9272	High Similarity	NPC210459
0.9272	High Similarity	NPC22192
0.9272	High Similarity	NPC55738
0.9267	High Similarity	NPC170026
0.9267	High Similarity	NPC201837
0.9267	High Similarity	NPC472626
0.9267	High Similarity	NPC209614
0.9267	High Similarity	NPC472916
0.9267	High Similarity	NPC470328
0.9267	High Similarity	NPC282307
0.9267	High Similarity	NPC250922
0.9262	High Similarity	NPC292214
0.9262	High Similarity	NPC273462
0.9262	High Similarity	NPC88645
0.9262	High Similarity	NPC206238
0.9262	High Similarity	NPC271779
0.9262	High Similarity	NPC167091
0.9262	High Similarity	NPC33051
0.9262	High Similarity	NPC227337
0.9262	High Similarity	NPC70433
0.9262	High Similarity	NPC49402
0.9257	High Similarity	NPC260895
0.9257	High Similarity	NPC125062
0.9257	High Similarity	NPC252933
0.9257	High Similarity	NPC154345
0.9257	High Similarity	NPC54394
0.9257	High Similarity	NPC251110
0.9257	High Similarity	NPC117579
0.9257	High Similarity	NPC200740
0.9252	High Similarity	NPC177298
0.9252	High Similarity	NPC264550
0.9252	High Similarity	NPC69430
0.9252	High Similarity	NPC195763
0.9252	High Similarity	NPC264289
0.9252	High Similarity	NPC200060
0.9252	High Similarity	NPC333691
0.9252	High Similarity	NPC38545
0.9252	High Similarity	NPC171916
0.9252	High Similarity	NPC142876
0.9252	High Similarity	NPC48479
0.9252	High Similarity	NPC139293
0.9252	High Similarity	NPC40290
0.9247	High Similarity	NPC275772
0.9247	High Similarity	NPC125449
0.9247	High Similarity	NPC207729
0.9247	High Similarity	NPC130230
0.9247	High Similarity	NPC12200
0.9247	High Similarity	NPC168803
0.9247	High Similarity	NPC239312
0.9247	High Similarity	NPC51443
0.9247	High Similarity	NPC188074
0.9247	High Similarity	NPC74881
0.9236	High Similarity	NPC471417
0.9236	High Similarity	NPC287722
0.9236	High Similarity	NPC202981
0.9236	High Similarity	NPC73028
0.9231	High Similarity	NPC76445
0.9231	High Similarity	NPC129853
0.9231	High Similarity	NPC182421
0.9231	High Similarity	NPC284550
0.9216	High Similarity	NPC474150
0.9216	High Similarity	NPC474162

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 NPC3036 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	946
0.2-0.3	1687
0.3-0.4	2656
0.4-0.5	1723
0.5-0.6	1066
0.6-0.7	508
0.7-0.8	128
0.8-0.85	30
0.85-0.9	15
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9589	High Similarity	NPD1934	Approved
0.9524	High Similarity	NPD2393	Clinical (unspecified phase)
0.9441	High Similarity	NPD1511	Approved
0.931	High Similarity	NPD1512	Approved
0.9155	High Similarity	NPD1552	Clinical (unspecified phase)
0.9155	High Similarity	NPD1550	Clinical (unspecified phase)
0.9133	High Similarity	NPD2801	Approved
0.9091	High Similarity	NPD1549	Phase 2
0.9013	High Similarity	NPD3882	Suspended
0.8974	High Similarity	NPD6168	Clinical (unspecified phase)
0.8974	High Similarity	NPD6166	Phase 2
0.8974	High Similarity	NPD6167	Clinical (unspecified phase)
0.8881	High Similarity	NPD1510	Phase 2
0.8766	High Similarity	NPD4868	Clinical (unspecified phase)
0.875	High Similarity	NPD7074	Phase 3
0.8742	High Similarity	NPD3818	Discontinued
0.8725	High Similarity	NPD4378	Clinical (unspecified phase)
0.8701	High Similarity	NPD3817	Phase 2
0.8688	High Similarity	NPD7054	Approved
0.8684	High Similarity	NPD4380	Phase 2
0.8634	High Similarity	NPD7472	Approved
0.8601	High Similarity	NPD943	Approved
0.8601	High Similarity	NPD1240	Approved
0.859	High Similarity	NPD4381	Clinical (unspecified phase)
0.859	High Similarity	NPD7075	Discontinued
0.8581	High Similarity	NPD8443	Clinical (unspecified phase)
0.858	High Similarity	NPD6797	Phase 2
0.8562	High Similarity	NPD2796	Approved
0.8528	High Similarity	NPD7251	Discontinued
0.8516	High Similarity	NPD7819	Suspended
0.8516	High Similarity	NPD7096	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD1607	Approved
0.8481	Intermediate Similarity	NPD5494	Approved
0.8476	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD6799	Approved
0.8387	Intermediate Similarity	NPD7411	Suspended
0.8364	Intermediate Similarity	NPD7808	Phase 3
0.8355	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1613	Approved
0.8345	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1465	Phase 2
0.8252	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7473	Discontinued
0.8217	Intermediate Similarity	NPD6801	Discontinued
0.8212	Intermediate Similarity	NPD3750	Approved
0.8205	Intermediate Similarity	NPD6599	Discontinued
0.8199	Intermediate Similarity	NPD6959	Discontinued
0.8188	Intermediate Similarity	NPD1551	Phase 2
0.8148	Intermediate Similarity	NPD6232	Discontinued
0.8125	Intermediate Similarity	NPD3749	Approved
0.8121	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD230	Phase 1
0.8013	Intermediate Similarity	NPD5403	Approved
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD5402	Approved
0.7976	Intermediate Similarity	NPD6559	Discontinued
0.7963	Intermediate Similarity	NPD919	Approved
0.7959	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1610	Phase 2
0.795	Intermediate Similarity	NPD7768	Phase 2
0.7947	Intermediate Similarity	NPD6099	Approved
0.7947	Intermediate Similarity	NPD6100	Approved
0.7908	Intermediate Similarity	NPD2800	Approved
0.7908	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3748	Approved
0.7881	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD3926	Phase 2
0.7866	Intermediate Similarity	NPD1247	Approved
0.7832	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2935	Discontinued
0.7823	Intermediate Similarity	NPD4908	Phase 1
0.7785	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2344	Approved
0.7771	Intermediate Similarity	NPD2533	Approved
0.7771	Intermediate Similarity	NPD2534	Approved
0.7771	Intermediate Similarity	NPD2532	Approved
0.777	Intermediate Similarity	NPD3027	Phase 3
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.7756	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6651	Approved
0.7742	Intermediate Similarity	NPD4628	Phase 3
0.7742	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1203	Approved
0.7719	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1933	Approved
0.7682	Intermediate Similarity	NPD447	Suspended
0.7677	Intermediate Similarity	NPD1243	Approved
0.7676	Intermediate Similarity	NPD1548	Phase 1
0.7673	Intermediate Similarity	NPD920	Approved
0.7665	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2799	Discontinued
0.7647	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD9494	Approved
0.7633	Intermediate Similarity	NPD3751	Discontinued
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5953	Discontinued
0.76	Intermediate Similarity	NPD2313	Discontinued
0.7595	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2309	Approved
0.7578	Intermediate Similarity	NPD3226	Approved
0.7569	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7534	Intermediate Similarity	NPD1608	Approved
0.753	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.7483	Intermediate Similarity	NPD3268	Approved
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6190	Approved
0.7467	Intermediate Similarity	NPD6832	Phase 2
0.7451	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2798	Approved
0.7419	Intermediate Similarity	NPD7033	Discontinued
0.7415	Intermediate Similarity	NPD9269	Phase 2
0.7415	Intermediate Similarity	NPD9717	Approved
0.74	Intermediate Similarity	NPD2861	Phase 2
0.7389	Intermediate Similarity	NPD4363	Phase 3
0.7389	Intermediate Similarity	NPD4360	Phase 2
0.7386	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2797	Approved
0.7375	Intermediate Similarity	NPD7390	Discontinued
0.7371	Intermediate Similarity	NPD8313	Approved
0.7371	Intermediate Similarity	NPD8312	Approved
0.7365	Intermediate Similarity	NPD4749	Approved
0.7362	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD422	Phase 1
0.7347	Intermediate Similarity	NPD1201	Approved
0.7333	Intermediate Similarity	NPD37	Approved
0.7329	Intermediate Similarity	NPD17	Approved
0.7329	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7228	Approved
0.7315	Intermediate Similarity	NPD3225	Approved
0.7308	Intermediate Similarity	NPD4308	Phase 3
0.7305	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7305	Intermediate Similarity	NPD4966	Approved
0.7303	Intermediate Similarity	NPD4625	Phase 3
0.7294	Intermediate Similarity	NPD5710	Approved
0.7294	Intermediate Similarity	NPD5711	Approved
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3267	Approved
0.7267	Intermediate Similarity	NPD1470	Approved
0.7267	Intermediate Similarity	NPD3266	Approved
0.7257	Intermediate Similarity	NPD7685	Pre-registration
0.7255	Intermediate Similarity	NPD411	Approved
0.7255	Intermediate Similarity	NPD6798	Discontinued
0.7255	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4361	Phase 2
0.7246	Intermediate Similarity	NPD4288	Approved
0.7233	Intermediate Similarity	NPD2654	Approved
0.7226	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5124	Phase 1
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7213	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7229	Phase 3
0.7192	Intermediate Similarity	NPD9545	Approved
0.7167	Intermediate Similarity	NPD4287	Approved
0.7161	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7151	Intermediate Similarity	NPD5242	Approved
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD9268	Approved
0.7126	Intermediate Similarity	NPD6844	Discontinued
0.711	Intermediate Similarity	NPD2403	Approved
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7081	Intermediate Similarity	NPD8166	Discontinued
0.7067	Intermediate Similarity	NPD3972	Approved
0.7062	Intermediate Similarity	NPD6104	Discontinued
0.7059	Intermediate Similarity	NPD3018	Phase 2
0.7056	Intermediate Similarity	NPD8150	Discontinued
0.7055	Intermediate Similarity	NPD9493	Approved
0.7053	Intermediate Similarity	NPD7584	Approved
0.7051	Intermediate Similarity	NPD4307	Phase 2
0.7045	Intermediate Similarity	NPD1729	Discontinued
0.7044	Intermediate Similarity	NPD5406	Approved
0.7044	Intermediate Similarity	NPD5404	Approved
0.7044	Intermediate Similarity	NPD5405	Approved
0.7044	Intermediate Similarity	NPD5408	Approved
0.7041	Intermediate Similarity	NPD2296	Approved
0.7037	Intermediate Similarity	NPD2354	Approved
0.7019	Intermediate Similarity	NPD1652	Phase 2
0.7012	Intermediate Similarity	NPD4662	Approved
0.7012	Intermediate Similarity	NPD4661	Approved
0.7007	Intermediate Similarity	NPD5536	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data