NPASS Compound

Structure

CID141212 OpenBabel06191715502D 22 24 0 0 1 0 0 0 0 0999 V2000 0.5176 1.9319 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 0.7765 2.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1907 1.4836 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 0.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 1.2247 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7424 3.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4495 2.4495 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 -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 1 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 2.0012 4.1225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4154 2.7083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 -0.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 9 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 16 1 0 0 0 0 8 22 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	1.772
LogD:	1.973
LogS:	-2.972
# 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:	0.624
Synthetic Accessibility Score:	3.225
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:	-5.118
MDCK Permeability:	9.83557492872933e-06
Pgp-inhibitor:	0.013
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.104
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	94.48245239257812%
Volume Distribution (VD):	0.564
Pgp-substrate:	5.016571521759033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.851
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.505
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.663
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.562
CYP2D6-substrate:	0.78
CYP3A4-inhibitor:	0.824
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	15.07
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.399
AMES Toxicity:	0.767
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.06
Skin Sensitization:	0.92
Carcinogencity:	0.345
Eye Corrosion:	0.003
Eye Irritation:	0.877
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC141212

Natural Product ID:	NPC141212
*Common Name:**	Sappanone B
IUPAC Name:	(3R)-3-[(3,4-dihydroxyphenyl)methyl]-3,7-dihydroxy-2H-chromen-4-one
Synonyms:
Standard InCHIKey:	BTLMXNHNFFXBHW-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C16H14O6/c17-10-2-3-11-14(6-10)22-8-16(21,15(11)20)7-9-1-4-12(18)13(19)5-9/h1-6,17-19,21H,7-8H2/t16-/m1/s1
SMILES:	c1cc(c(cc1C[C@]1(COc2cc(ccc2C1=O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477778
PubChem CID:	13888976
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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
NPO32846	heamatoxylon campechianum	Species	n.a.	n.a.	stems	XiShuangBanNa, Yunnan Province, China	2005-Sep	PMID[18610999]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2554	Biancaea sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2554	Biancaea sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2554	Biancaea sappan	Species	Fabaceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	=	82.1	%	PMID[458866]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Inhibition	=	54.2	%	PMID[458866]

☑ 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 NPC141212 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	427
0.1-0.2	1791
0.2-0.3	4634
0.3-0.4	10639
0.4-0.5	6868
0.5-0.6	3514
0.6-0.7	4876
0.7-0.8	5349
0.8-0.85	2569
0.85-0.9	1435
0.9-0.95	553
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC474638
0.9799	High Similarity	NPC67876
0.9733	High Similarity	NPC55738
0.973	High Similarity	NPC325028
0.973	High Similarity	NPC246328
0.973	High Similarity	NPC27532
0.973	High Similarity	NPC256346
0.9667	High Similarity	NPC52530
0.9662	High Similarity	NPC36835
0.9662	High Similarity	NPC240476
0.9662	High Similarity	NPC260491
0.9662	High Similarity	NPC9743
0.9662	High Similarity	NPC246162
0.9662	High Similarity	NPC61506
0.96	High Similarity	NPC320825
0.96	High Similarity	NPC326037
0.96	High Similarity	NPC13858
0.96	High Similarity	NPC471500
0.9592	High Similarity	NPC105512
0.9592	High Similarity	NPC1612
0.9592	High Similarity	NPC183959
0.9589	High Similarity	NPC95864
0.9539	High Similarity	NPC470183
0.9536	High Similarity	NPC471479
0.9536	High Similarity	NPC471515
0.953	High Similarity	NPC19721
0.953	High Similarity	NPC55205
0.953	High Similarity	NPC219582
0.953	High Similarity	NPC302950
0.953	High Similarity	NPC236637
0.9524	High Similarity	NPC321011
0.9524	High Similarity	NPC294852
0.9524	High Similarity	NPC188679
0.9524	High Similarity	NPC3036
0.9521	High Similarity	NPC229190
0.9477	High Similarity	NPC308992
0.9477	High Similarity	NPC173137
0.9474	High Similarity	NPC22192
0.9474	High Similarity	NPC152904
0.947	High Similarity	NPC201837
0.947	High Similarity	NPC250922
0.9467	High Similarity	NPC18727
0.9467	High Similarity	NPC469550
0.9463	High Similarity	NPC125062
0.9463	High Similarity	NPC260895
0.9463	High Similarity	NPC54394
0.9463	High Similarity	NPC252933
0.9463	High Similarity	NPC200740
0.9463	High Similarity	NPC31363
0.9459	High Similarity	NPC87125
0.9459	High Similarity	NPC270465
0.9456	High Similarity	NPC74881
0.9456	High Similarity	NPC51443
0.9412	High Similarity	NPC471744
0.9412	High Similarity	NPC263449
0.9412	High Similarity	NPC282009
0.9412	High Similarity	NPC287328
0.9408	High Similarity	NPC299520
0.9408	High Similarity	NPC27337
0.9408	High Similarity	NPC210084
0.9408	High Similarity	NPC129684
0.9408	High Similarity	NPC291508
0.9408	High Similarity	NPC99597
0.9404	High Similarity	NPC2928
0.94	High Similarity	NPC82325
0.94	High Similarity	NPC477231
0.94	High Similarity	NPC472912
0.94	High Similarity	NPC260979
0.94	High Similarity	NPC257648
0.94	High Similarity	NPC279989
0.9396	High Similarity	NPC267117
0.9396	High Similarity	NPC29231
0.9396	High Similarity	NPC149127
0.9396	High Similarity	NPC286342
0.9396	High Similarity	NPC188871
0.9392	High Similarity	NPC196277
0.9392	High Similarity	NPC43669
0.9392	High Similarity	NPC272721
0.9392	High Similarity	NPC119059
0.9392	High Similarity	NPC218569
0.9388	High Similarity	NPC179271
0.9388	High Similarity	NPC20791
0.9355	High Similarity	NPC472625
0.9351	High Similarity	NPC112418
0.9351	High Similarity	NPC471499
0.9351	High Similarity	NPC289771
0.9342	High Similarity	NPC303255
0.9342	High Similarity	NPC195796
0.9342	High Similarity	NPC235165
0.9342	High Similarity	NPC472916
0.9342	High Similarity	NPC35038
0.9342	High Similarity	NPC265511
0.9342	High Similarity	NPC24640
0.9342	High Similarity	NPC291878
0.9342	High Similarity	NPC255106
0.9342	High Similarity	NPC278778
0.9338	High Similarity	NPC167091
0.9338	High Similarity	NPC270620
0.9338	High Similarity	NPC271779
0.9338	High Similarity	NPC192083
0.9338	High Similarity	NPC179126
0.9338	High Similarity	NPC78326
0.9338	High Similarity	NPC206238
0.9338	High Similarity	NPC236223
0.9338	High Similarity	NPC88645
0.9338	High Similarity	NPC292214
0.9338	High Similarity	NPC74924
0.9338	High Similarity	NPC213896
0.9333	High Similarity	NPC251110
0.9333	High Similarity	NPC50403
0.9333	High Similarity	NPC471229
0.9333	High Similarity	NPC133953
0.9333	High Similarity	NPC28274
0.9333	High Similarity	NPC204515
0.9329	High Similarity	NPC52005
0.9329	High Similarity	NPC223579
0.9329	High Similarity	NPC277032
0.9329	High Similarity	NPC137062
0.9329	High Similarity	NPC159103
0.9329	High Similarity	NPC183950
0.9329	High Similarity	NPC287101
0.9324	High Similarity	NPC77378
0.9324	High Similarity	NPC108406
0.9324	High Similarity	NPC21835
0.9324	High Similarity	NPC472918
0.932	High Similarity	NPC70136
0.9295	High Similarity	NPC234052
0.9295	High Similarity	NPC62261
0.9295	High Similarity	NPC224280
0.929	High Similarity	NPC474034
0.929	High Similarity	NPC472964
0.929	High Similarity	NPC471745
0.929	High Similarity	NPC474033
0.9286	High Similarity	NPC118256
0.9286	High Similarity	NPC470326
0.9286	High Similarity	NPC472902
0.9286	High Similarity	NPC474960
0.9286	High Similarity	NPC119209
0.9286	High Similarity	NPC328102
0.9286	High Similarity	NPC472624
0.9286	High Similarity	NPC192686
0.9281	High Similarity	NPC96167
0.9281	High Similarity	NPC156057
0.9281	High Similarity	NPC472913
0.9281	High Similarity	NPC162869
0.9281	High Similarity	NPC472598
0.9281	High Similarity	NPC472914
0.9281	High Similarity	NPC222814
0.9281	High Similarity	NPC472963
0.9281	High Similarity	NPC48208
0.9281	High Similarity	NPC474055
0.9281	High Similarity	NPC474836
0.9281	High Similarity	NPC474208
0.9281	High Similarity	NPC475267
0.9281	High Similarity	NPC52889
0.9281	High Similarity	NPC472911
0.9281	High Similarity	NPC472910
0.9281	High Similarity	NPC245758
0.9281	High Similarity	NPC471209
0.9276	High Similarity	NPC234255
0.9276	High Similarity	NPC45849
0.9276	High Similarity	NPC200761
0.9276	High Similarity	NPC256925
0.9276	High Similarity	NPC67396
0.9276	High Similarity	NPC168247
0.9276	High Similarity	NPC133392
0.9276	High Similarity	NPC26227
0.9276	High Similarity	NPC31018
0.9276	High Similarity	NPC201451
0.9276	High Similarity	NPC117992
0.9276	High Similarity	NPC321779
0.9276	High Similarity	NPC255807
0.9276	High Similarity	NPC152951
0.9276	High Similarity	NPC230149
0.9276	High Similarity	NPC470327
0.9276	High Similarity	NPC477503
0.9276	High Similarity	NPC57674
0.9276	High Similarity	NPC44079
0.9272	High Similarity	NPC63187
0.9272	High Similarity	NPC37684
0.9272	High Similarity	NPC123886
0.9272	High Similarity	NPC120537
0.9272	High Similarity	NPC39732
0.9272	High Similarity	NPC180234
0.9272	High Similarity	NPC39007
0.9272	High Similarity	NPC106976
0.9272	High Similarity	NPC161277
0.9272	High Similarity	NPC304954
0.9272	High Similarity	NPC157784
0.9272	High Similarity	NPC101996
0.9272	High Similarity	NPC60972
0.9272	High Similarity	NPC199100
0.9267	High Similarity	NPC166753
0.9267	High Similarity	NPC248102
0.9267	High Similarity	NPC62042
0.9267	High Similarity	NPC50728
0.9267	High Similarity	NPC61620
0.9267	High Similarity	NPC338131
0.9262	High Similarity	NPC80710
0.9262	High Similarity	NPC254702

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 NPC141212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	951
0.2-0.3	1817
0.3-0.4	2581
0.4-0.5	1744
0.5-0.6	1007
0.6-0.7	448
0.7-0.8	135
0.8-0.85	37
0.85-0.9	11
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.953	High Similarity	NPD1934	Approved
0.9388	High Similarity	NPD1512	Approved
0.9338	High Similarity	NPD2393	Clinical (unspecified phase)
0.9252	High Similarity	NPD1511	Approved
0.9216	High Similarity	NPD3882	Suspended
0.9172	High Similarity	NPD6166	Phase 2
0.9172	High Similarity	NPD6168	Clinical (unspecified phase)
0.9172	High Similarity	NPD6167	Clinical (unspecified phase)
0.9085	High Similarity	NPD2801	Approved
0.8912	High Similarity	NPD1549	Phase 2
0.8903	High Similarity	NPD3817	Phase 2
0.8846	High Similarity	NPD4868	Clinical (unspecified phase)
0.8844	High Similarity	NPD1552	Clinical (unspecified phase)
0.8844	High Similarity	NPD1550	Clinical (unspecified phase)
0.882	High Similarity	NPD3818	Discontinued
0.8808	High Similarity	NPD4378	Clinical (unspecified phase)
0.879	High Similarity	NPD7075	Discontinued
0.8773	High Similarity	NPD6797	Phase 2
0.8766	High Similarity	NPD4380	Phase 2
0.872	High Similarity	NPD7251	Discontinued
0.8718	High Similarity	NPD7096	Clinical (unspecified phase)
0.8712	High Similarity	NPD7074	Phase 3
0.8707	High Similarity	NPD1510	Phase 2
0.8671	High Similarity	NPD4381	Clinical (unspecified phase)
0.8667	High Similarity	NPD4338	Clinical (unspecified phase)
0.865	High Similarity	NPD7054	Approved
0.8618	High Similarity	NPD6799	Approved
0.8598	High Similarity	NPD7472	Approved
0.8554	High Similarity	NPD7808	Phase 3
0.8545	High Similarity	NPD7993	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD5494	Approved
0.8435	Intermediate Similarity	NPD943	Approved
0.8435	Intermediate Similarity	NPD1240	Approved
0.8418	Intermediate Similarity	NPD6801	Discontinued
0.8408	Intermediate Similarity	NPD6599	Discontinued
0.84	Intermediate Similarity	NPD2796	Approved
0.8365	Intermediate Similarity	NPD1465	Phase 2
0.8365	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1607	Approved
0.8313	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5402	Approved
0.8311	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1613	Approved
0.8288	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7411	Suspended
0.8219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5403	Approved
0.8205	Intermediate Similarity	NPD5401	Approved
0.8199	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD1247	Approved
0.816	Intermediate Similarity	NPD919	Approved
0.8121	Intermediate Similarity	NPD6232	Discontinued
0.8098	Intermediate Similarity	NPD3749	Approved
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8092	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7473	Discontinued
0.8072	Intermediate Similarity	NPD3926	Phase 2
0.8065	Intermediate Similarity	NPD3750	Approved
0.8061	Intermediate Similarity	NPD6959	Discontinued
0.8059	Intermediate Similarity	NPD6559	Discontinued
0.8039	Intermediate Similarity	NPD1551	Phase 2
0.8036	Intermediate Similarity	NPD3751	Discontinued
0.8013	Intermediate Similarity	NPD230	Phase 1
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6190	Approved
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7806	Intermediate Similarity	NPD2935	Discontinued
0.7798	Intermediate Similarity	NPD3787	Discontinued
0.7778	Intermediate Similarity	NPD447	Suspended
0.7771	Intermediate Similarity	NPD2800	Approved
0.7771	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD3027	Phase 3
0.7742	Intermediate Similarity	NPD3748	Approved
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6099	Approved
0.7692	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1933	Approved
0.7654	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD920	Approved
0.7647	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2344	Approved
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2534	Approved
0.7625	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD9494	Approved
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1653	Approved
0.76	Intermediate Similarity	NPD1203	Approved
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.7568	Intermediate Similarity	NPD1610	Phase 2
0.7561	Intermediate Similarity	NPD3226	Approved
0.7554	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1243	Approved
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7471	Intermediate Similarity	NPD7286	Phase 2
0.7469	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2309	Approved
0.7451	Intermediate Similarity	NPD4908	Phase 1
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7401	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD9269	Phase 2
0.7391	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6651	Approved
0.7366	Intermediate Similarity	NPD6777	Approved
0.7366	Intermediate Similarity	NPD6780	Approved
0.7366	Intermediate Similarity	NPD6776	Approved
0.7366	Intermediate Similarity	NPD6778	Approved
0.7366	Intermediate Similarity	NPD6781	Approved
0.7366	Intermediate Similarity	NPD6782	Approved
0.7366	Intermediate Similarity	NPD6779	Approved
0.736	Intermediate Similarity	NPD8313	Approved
0.736	Intermediate Similarity	NPD8312	Approved
0.7355	Intermediate Similarity	NPD6798	Discontinued
0.7355	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2354	Approved
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD8150	Discontinued
0.7317	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2403	Approved
0.7296	Intermediate Similarity	NPD7033	Discontinued
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.7285	Intermediate Similarity	NPD9717	Approved
0.7256	Intermediate Similarity	NPD7390	Discontinued
0.7249	Intermediate Similarity	NPD7435	Discontinued
0.7241	Intermediate Similarity	NPD5242	Approved
0.7225	Intermediate Similarity	NPD7584	Approved
0.7219	Intermediate Similarity	NPD37	Approved
0.7216	Intermediate Similarity	NPD7228	Approved
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7208	Intermediate Similarity	NPD2798	Approved
0.7197	Intermediate Similarity	NPD6233	Phase 2
0.7193	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD4965	Approved
0.7193	Intermediate Similarity	NPD4967	Phase 2
0.7189	Intermediate Similarity	NPD4363	Phase 3
0.7189	Intermediate Similarity	NPD4360	Phase 2
0.7184	Intermediate Similarity	NPD5711	Approved
0.7184	Intermediate Similarity	NPD5710	Approved
0.7179	Intermediate Similarity	NPD4625	Phase 3
0.7171	Intermediate Similarity	NPD1608	Approved
0.7161	Intermediate Similarity	NPD2861	Phase 2
0.7158	Intermediate Similarity	NPD7698	Approved
0.7158	Intermediate Similarity	NPD4287	Approved
0.7158	Intermediate Similarity	NPD7696	Phase 3
0.7158	Intermediate Similarity	NPD7697	Approved
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1470	Approved
0.7135	Intermediate Similarity	NPD5353	Approved
0.7135	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD3887	Approved
0.7134	Intermediate Similarity	NPD3764	Approved
0.7134	Intermediate Similarity	NPD411	Approved
0.7133	Intermediate Similarity	NPD9268	Approved
0.7124	Intermediate Similarity	NPD4749	Approved
0.712	Intermediate Similarity	NPD7871	Phase 2
0.712	Intermediate Similarity	NPD7870	Phase 2
0.7118	Intermediate Similarity	NPD6844	Discontinued
0.7108	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD422	Phase 1
0.7105	Intermediate Similarity	NPD1201	Approved
0.7102	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2353	Approved
0.7099	Intermediate Similarity	NPD1471	Phase 3
0.7099	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7266	Discontinued
0.7098	Intermediate Similarity	NPD7701	Phase 2
0.7097	Intermediate Similarity	NPD6534	Approved
0.7097	Intermediate Similarity	NPD6535	Approved
0.7093	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3225	Approved
0.707	Intermediate Similarity	NPD7095	Approved
0.7067	Intermediate Similarity	NPD9545	Approved
0.7066	Intermediate Similarity	NPD5049	Phase 3
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6385	Approved
0.7059	Intermediate Similarity	NPD6386	Approved
0.7055	Intermediate Similarity	NPD2424	Discontinued
0.7044	Intermediate Similarity	NPD4307	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