NPASS Compound

Structure

NPC469953 OpenBabel07101718312D 32 34 0 0 0 0 0 0 0 0999 V2000 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -3.4641 3.0000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 0.8660 4.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 31 1 0 0 0 0 6 15 2 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 16 2 0 0 0 0 11 16 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 26 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 17 24 1 0 0 0 0 17 25 2 0 0 0 0 18 20 1 0 0 0 0 19 27 2 0 0 0 0 19 28 1 0 0 0 0 20 23 2 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 22 29 2 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.17
Volume:	456.323
LogP:	5.08
LogD:	3.531
LogS:	-4.011
# Rotatable Bonds:	6
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	3.261
Fsp3:	0.231
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:	-4.974
MDCK Permeability:	1.2175421943538822e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.083

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	100.4542007446289%
Volume Distribution (VD):	0.283
Pgp-substrate:	1.1337244510650635%

ADMET: Metabolism

CYP1A2-inhibitor:	0.309
CYP1A2-substrate:	0.756
CYP2C19-inhibitor:	0.134
CYP2C19-substrate:	0.122
CYP2C9-inhibitor:	0.9
CYP2C9-substrate:	0.301
CYP2D6-inhibitor:	0.837
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.362
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	0.754
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.287
Carcinogencity:	0.731
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.675

Download Data

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

Natural Product: NPC469953

Natural Product ID:	NPC469953
*Common Name:**	3-[7-Hydroxy-5-Methoxy-2,2-Dimethyl-6-(2-Methyl-But-2-Enoyl)-2H-Chromen-8-Yl]-3-Phenyl-Acrylic Acid
IUPAC Name:	(E)-3-[7-hydroxy-5-methoxy-2,2-dimethyl-6-[(E)-2-methylbut-2-enoyl]chromen-8-yl]-3-phenylprop-2-enoic acid
Synonyms:
Standard InCHIKey:	ITDQXOISWWDOGP-MSBMPMNRSA-N
Standard InCHI:	InChI=1S/C26H26O6/c1-6-15(2)22(29)21-23(30)20(18(14-19(27)28)16-10-8-7-9-11-16)25-17(24(21)31-5)12-13-26(3,4)32-25/h6-14,30H,1-5H3,(H,27,28)/b15-6+,18-14+
SMILES:	C/C=C(/C(=O)c1c(O)c(/C(=C/C(=O)O)/c2ccccc2)c2c(c1OC)C=CC(O2)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL133575
PubChem CID:	44354054
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-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
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	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
IC50	4
Others	2

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	100000.0	nM	PMID[479016]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	4500.0	nM	PMID[479016]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	36400.0	nM	PMID[479017]
NPT886	Cell Line	NIH3T3	Mus musculus	CC50	=	41100.0	nM	PMID[479017]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2200.0	nM	PMID[479017]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	19.2	n.a.	PMID[479017]

☑ 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 NPC469953 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	338
0.1-0.2	1535
0.2-0.3	3723
0.3-0.4	8949
0.4-0.5	9527
0.5-0.6	3652
0.6-0.7	5955
0.7-0.8	5228
0.8-0.85	2060
0.85-0.9	1192
0.9-0.95	510
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC180477
0.9712	High Similarity	NPC36181
0.9712	High Similarity	NPC226636
0.9712	High Similarity	NPC11561
0.9645	High Similarity	NPC57470
0.9645	High Similarity	NPC470322
0.9643	High Similarity	NPC94794
0.9643	High Similarity	NPC188632
0.9643	High Similarity	NPC112791
0.9643	High Similarity	NPC196459
0.9643	High Similarity	NPC87609
0.9643	High Similarity	NPC470296
0.964	High Similarity	NPC205006
0.964	High Similarity	NPC147688
0.964	High Similarity	NPC110969
0.964	High Similarity	NPC103362
0.964	High Similarity	NPC156590
0.964	High Similarity	NPC64908
0.964	High Similarity	NPC118840
0.9638	High Similarity	NPC217186
0.9638	High Similarity	NPC53181
0.958	High Similarity	NPC104236
0.958	High Similarity	NPC164205
0.9577	High Similarity	NPC249942
0.9577	High Similarity	NPC297886
0.9577	High Similarity	NPC140120
0.9574	High Similarity	NPC178627
0.9574	High Similarity	NPC311741
0.9574	High Similarity	NPC196137
0.9574	High Similarity	NPC469935
0.9574	High Similarity	NPC1886
0.9574	High Similarity	NPC234629
0.9568	High Similarity	NPC475680
0.9568	High Similarity	NPC235239
0.9568	High Similarity	NPC261227
0.9568	High Similarity	NPC241100
0.9568	High Similarity	NPC159275
0.9568	High Similarity	NPC172986
0.9568	High Similarity	NPC270883
0.9568	High Similarity	NPC305355
0.9568	High Similarity	NPC150522
0.9514	High Similarity	NPC151973
0.951	High Similarity	NPC469933
0.951	High Similarity	NPC161864
0.951	High Similarity	NPC208303
0.9507	High Similarity	NPC181388
0.9507	High Similarity	NPC154217
0.9504	High Similarity	NPC18585
0.9504	High Similarity	NPC166138
0.9504	High Similarity	NPC106985
0.9504	High Similarity	NPC38219
0.95	High Similarity	NPC282300
0.9496	High Similarity	NPC301217
0.9496	High Similarity	NPC220062
0.9496	High Similarity	NPC78913
0.9496	High Similarity	NPC96565
0.9496	High Similarity	NPC216978
0.9496	High Similarity	NPC303633
0.9496	High Similarity	NPC55018
0.9496	High Similarity	NPC18260
0.9444	High Similarity	NPC469932
0.9444	High Similarity	NPC19238
0.9441	High Similarity	NPC23728
0.9441	High Similarity	NPC104406
0.9441	High Similarity	NPC24673
0.9441	High Similarity	NPC79469
0.9441	High Similarity	NPC201731
0.9441	High Similarity	NPC110303
0.9441	High Similarity	NPC97716
0.9441	High Similarity	NPC237635
0.9437	High Similarity	NPC209040
0.9437	High Similarity	NPC278175
0.9437	High Similarity	NPC257236
0.9433	High Similarity	NPC59739
0.9433	High Similarity	NPC78803
0.9433	High Similarity	NPC266725
0.9433	High Similarity	NPC214236
0.9433	High Similarity	NPC293852
0.9433	High Similarity	NPC62840
0.9433	High Similarity	NPC144499
0.9433	High Similarity	NPC217083
0.9433	High Similarity	NPC299080
0.9429	High Similarity	NPC221173
0.9429	High Similarity	NPC69769
0.9424	High Similarity	NPC272844
0.9424	High Similarity	NPC201395
0.9424	High Similarity	NPC248995
0.9424	High Similarity	NPC254168
0.9379	High Similarity	NPC474735
0.9375	High Similarity	NPC266572
0.9375	High Similarity	NPC132592
0.9375	High Similarity	NPC160821
0.9375	High Similarity	NPC6511
0.9371	High Similarity	NPC312973
0.9371	High Similarity	NPC88964
0.9371	High Similarity	NPC470647
0.9371	High Similarity	NPC83357
0.9371	High Similarity	NPC142405
0.9371	High Similarity	NPC54577
0.9371	High Similarity	NPC477955
0.9371	High Similarity	NPC475052
0.9371	High Similarity	NPC20488
0.9371	High Similarity	NPC246948
0.9371	High Similarity	NPC67805
0.9371	High Similarity	NPC301276
0.9371	High Similarity	NPC111786
0.9371	High Similarity	NPC195621
0.9371	High Similarity	NPC124729
0.9371	High Similarity	NPC267375
0.9371	High Similarity	NPC176229
0.9371	High Similarity	NPC214774
0.9366	High Similarity	NPC214166
0.9366	High Similarity	NPC91560
0.9366	High Similarity	NPC75049
0.9366	High Similarity	NPC221432
0.9366	High Similarity	NPC164980
0.9366	High Similarity	NPC68104
0.9366	High Similarity	NPC219915
0.9366	High Similarity	NPC169591
0.9366	High Similarity	NPC316816
0.9366	High Similarity	NPC175504
0.9366	High Similarity	NPC39329
0.9366	High Similarity	NPC149026
0.9366	High Similarity	NPC478086
0.9366	High Similarity	NPC310130
0.9366	High Similarity	NPC257097
0.9366	High Similarity	NPC143896
0.9366	High Similarity	NPC150408
0.9362	High Similarity	NPC110038
0.9362	High Similarity	NPC3188
0.9362	High Similarity	NPC248372
0.9362	High Similarity	NPC470555
0.9357	High Similarity	NPC472343
0.9357	High Similarity	NPC240305
0.9357	High Similarity	NPC283429
0.9357	High Similarity	NPC23257
0.9353	High Similarity	NPC317119
0.9353	High Similarity	NPC266597
0.9353	High Similarity	NPC250266
0.9348	High Similarity	NPC101752
0.9348	High Similarity	NPC156092
0.9315	High Similarity	NPC290671
0.9306	High Similarity	NPC283234
0.9306	High Similarity	NPC296998
0.9306	High Similarity	NPC473077
0.9301	High Similarity	NPC131568
0.9301	High Similarity	NPC236766
0.9301	High Similarity	NPC319752
0.9301	High Similarity	NPC473015
0.9301	High Similarity	NPC197252
0.9301	High Similarity	NPC273538
0.9301	High Similarity	NPC131579
0.9301	High Similarity	NPC473013
0.9301	High Similarity	NPC216538
0.9296	High Similarity	NPC10937
0.9296	High Similarity	NPC64915
0.9296	High Similarity	NPC324134
0.9296	High Similarity	NPC227579
0.9296	High Similarity	NPC37496
0.9296	High Similarity	NPC324436
0.9296	High Similarity	NPC223500
0.9296	High Similarity	NPC328164
0.9296	High Similarity	NPC40833
0.9296	High Similarity	NPC265040
0.9296	High Similarity	NPC76338
0.9296	High Similarity	NPC1089
0.9296	High Similarity	NPC296917
0.9296	High Similarity	NPC161506
0.9296	High Similarity	NPC32739
0.9296	High Similarity	NPC200694
0.9296	High Similarity	NPC78
0.9296	High Similarity	NPC66515
0.9296	High Similarity	NPC306829
0.9296	High Similarity	NPC194432
0.9296	High Similarity	NPC166482
0.9296	High Similarity	NPC177354
0.9296	High Similarity	NPC220998
0.9296	High Similarity	NPC125855
0.9296	High Similarity	NPC182852
0.9296	High Similarity	NPC107572
0.9296	High Similarity	NPC76372
0.9296	High Similarity	NPC228504
0.9296	High Similarity	NPC147145
0.9296	High Similarity	NPC148757
0.9296	High Similarity	NPC166934
0.9296	High Similarity	NPC167624
0.9291	High Similarity	NPC219917
0.9291	High Similarity	NPC471587
0.9291	High Similarity	NPC215311
0.9291	High Similarity	NPC213659
0.9291	High Similarity	NPC144118
0.9291	High Similarity	NPC80962
0.9291	High Similarity	NPC172250
0.9291	High Similarity	NPC259166
0.9291	High Similarity	NPC204985
0.9291	High Similarity	NPC48624
0.9291	High Similarity	NPC326109
0.9286	High Similarity	NPC470669
0.9286	High Similarity	NPC21350
0.9286	High Similarity	NPC124269

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 NPC469953 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	944
0.2-0.3	1505
0.3-0.4	2530
0.4-0.5	1997
0.5-0.6	1220
0.6-0.7	423
0.7-0.8	157
0.8-0.85	44
0.85-0.9	18
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9437	High Similarity	NPD7410	Clinical (unspecified phase)
0.9301	High Similarity	NPD4378	Clinical (unspecified phase)
0.9184	High Similarity	NPD7411	Suspended
0.9014	High Similarity	NPD1549	Phase 2
0.9007	High Similarity	NPD7075	Discontinued
0.8993	High Similarity	NPD6801	Discontinued
0.8944	High Similarity	NPD1552	Clinical (unspecified phase)
0.8944	High Similarity	NPD1550	Clinical (unspecified phase)
0.8936	High Similarity	NPD1510	Phase 2
0.8933	High Similarity	NPD7096	Clinical (unspecified phase)
0.8933	High Similarity	NPD7819	Suspended
0.8921	High Similarity	NPD1240	Approved
0.8873	High Similarity	NPD2796	Approved
0.8836	High Similarity	NPD6799	Approved
0.8819	High Similarity	NPD7421	Clinical (unspecified phase)
0.8794	High Similarity	NPD1607	Approved
0.8759	High Similarity	NPD3750	Approved
0.8733	High Similarity	NPD4380	Phase 2
0.8693	High Similarity	NPD7768	Phase 2
0.8684	High Similarity	NPD2393	Clinical (unspecified phase)
0.8662	High Similarity	NPD7852	Clinical (unspecified phase)
0.8627	High Similarity	NPD8443	Clinical (unspecified phase)
0.8609	High Similarity	NPD6599	Discontinued
0.8562	High Similarity	NPD1243	Approved
0.8516	High Similarity	NPD3749	Approved
0.8516	High Similarity	NPD4381	Clinical (unspecified phase)
0.8511	High Similarity	NPD2313	Discontinued
0.8511	High Similarity	NPD6859	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD2935	Discontinued
0.8483	Intermediate Similarity	NPD1551	Phase 2
0.8456	Intermediate Similarity	NPD1511	Approved
0.8442	Intermediate Similarity	NPD2801	Approved
0.8414	Intermediate Similarity	NPD2799	Discontinued
0.8414	Intermediate Similarity	NPD3748	Approved
0.8411	Intermediate Similarity	NPD5403	Approved
0.8411	Intermediate Similarity	NPD920	Approved
0.8389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD3817	Phase 2
0.8377	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD1512	Approved
0.8311	Intermediate Similarity	NPD2800	Approved
0.8286	Intermediate Similarity	NPD1203	Approved
0.8282	Intermediate Similarity	NPD5953	Discontinued
0.8278	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD2532	Approved
0.8278	Intermediate Similarity	NPD5401	Approved
0.8278	Intermediate Similarity	NPD2534	Approved
0.8278	Intermediate Similarity	NPD2533	Approved
0.8276	Intermediate Similarity	NPD6651	Approved
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7286	Phase 2
0.8255	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD3882	Suspended
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8163	Intermediate Similarity	NPD7033	Discontinued
0.8148	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD3268	Approved
0.8125	Intermediate Similarity	NPD6959	Discontinued
0.8112	Intermediate Similarity	NPD6832	Phase 2
0.8101	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD3818	Discontinued
0.8082	Intermediate Similarity	NPD5124	Phase 1
0.8082	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD9717	Approved
0.8065	Intermediate Similarity	NPD3226	Approved
0.8054	Intermediate Similarity	NPD2346	Discontinued
0.8041	Intermediate Similarity	NPD4308	Phase 3
0.8038	Intermediate Similarity	NPD5402	Approved
0.8028	Intermediate Similarity	NPD2797	Approved
0.8013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD919	Approved
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD5494	Approved
0.7939	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD7054	Approved
0.7933	Intermediate Similarity	NPD2344	Approved
0.7892	Intermediate Similarity	NPD7472	Approved
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7857	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD2798	Approved
0.7844	Intermediate Similarity	NPD6797	Phase 2
0.7832	Intermediate Similarity	NPD3225	Approved
0.7829	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7785	Intermediate Similarity	NPD6585	Discontinued
0.7778	Intermediate Similarity	NPD3267	Approved
0.7778	Intermediate Similarity	NPD3266	Approved
0.777	Intermediate Similarity	NPD4307	Phase 2
0.7755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7748	Intermediate Similarity	NPD6100	Approved
0.7748	Intermediate Similarity	NPD6099	Approved
0.7746	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5889	Approved
0.7736	Intermediate Similarity	NPD5890	Approved
0.7727	Intermediate Similarity	NPD2309	Approved
0.7718	Intermediate Similarity	NPD1933	Approved
0.7714	Intermediate Similarity	NPD1548	Phase 1
0.7714	Intermediate Similarity	NPD9545	Approved
0.7707	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD4288	Approved
0.7698	Intermediate Similarity	NPD9493	Approved
0.7651	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD5049	Phase 3
0.764	Intermediate Similarity	NPD1465	Phase 2
0.7636	Intermediate Similarity	NPD5711	Approved
0.7636	Intermediate Similarity	NPD5710	Approved
0.7635	Intermediate Similarity	NPD1296	Phase 2
0.7635	Intermediate Similarity	NPD3764	Approved
0.7633	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5405	Approved
0.7632	Intermediate Similarity	NPD5406	Approved
0.7632	Intermediate Similarity	NPD5408	Approved
0.7632	Intermediate Similarity	NPD5404	Approved
0.7619	Intermediate Similarity	NPD4908	Phase 1
0.761	Intermediate Similarity	NPD7458	Discontinued
0.76	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4287	Approved
0.7582	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1247	Approved
0.7569	Intermediate Similarity	NPD1608	Approved
0.7548	Intermediate Similarity	NPD7003	Approved
0.7534	Intermediate Similarity	NPD1164	Approved
0.7517	Intermediate Similarity	NPD6798	Discontinued
0.7517	Intermediate Similarity	NPD411	Approved
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD2354	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7484	Intermediate Similarity	NPD2654	Approved
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD1019	Discontinued
0.7472	Intermediate Similarity	NPD4361	Phase 2
0.7472	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1729	Discontinued
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4625	Phase 3
0.7448	Intermediate Similarity	NPD3972	Approved
0.744	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7229	Phase 3
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3887	Approved
0.7361	Intermediate Similarity	NPD17	Approved
0.7355	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2353	Approved
0.7353	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7584	Approved
0.7343	Intermediate Similarity	NPD1894	Discontinued
0.7329	Intermediate Similarity	NPD1481	Phase 2
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.729	Intermediate Similarity	NPD4476	Approved
0.729	Intermediate Similarity	NPD4477	Approved
0.7289	Intermediate Similarity	NPD6971	Discontinued
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7199	Phase 2
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.726	Intermediate Similarity	NPD1535	Discovery
0.7255	Intermediate Similarity	NPD6355	Discontinued
0.7251	Intermediate Similarity	NPD7177	Discontinued
0.7244	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6005	Phase 3
0.7244	Intermediate Similarity	NPD6004	Phase 3
0.7244	Intermediate Similarity	NPD6002	Phase 3
0.7244	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6233	Phase 2
0.7234	Intermediate Similarity	NPD1241	Discontinued
0.7233	Intermediate Similarity	NPD7440	Discontinued
0.7213	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6273	Approved
0.7191	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4060	Phase 1
0.7184	Intermediate Similarity	NPD6104	Discontinued
0.7181	Intermediate Similarity	NPD1470	Approved
0.7176	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2296	Approved
0.7163	Intermediate Similarity	NPD5535	Approved
0.7162	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1201	Approved
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7134	Intermediate Similarity	NPD6502	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