NPASS Compound

Structure

NPC472662 OpenBabel07101719512D 27 32 0 0 1 0 0 0 0 0999 V2000 -0.3838 -0.0601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5020 -4.3905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4531 -2.6995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0409 -1.8905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6360 0.1095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7700 -2.3905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1061 -1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7090 -0.1843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5020 -2.3905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6360 -0.8905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7700 -1.3905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6360 -2.8905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7700 0.6095 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5020 -1.3905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9039 0.1095 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4898 0.2909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5675 1.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1608 0.7786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9039 -0.8905 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5141 -0.5219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3774 0.7515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0675 2.5582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3341 -1.0943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6360 -3.8905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4531 -1.0815 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 1.5621 1.5876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 25 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 20 1 0 0 0 0 8 19 1 0 0 0 0 8 26 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 19 1 0 0 0 0 12 24 1 0 0 0 0 13 5 1 6 0 0 0 13 15 1 0 0 0 0 13 27 1 0 0 0 0 14 25 1 0 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 18 1 6 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 17 27 1 0 0 0 0 18 1 1 1 0 0 0 19 7 1 1 0 0 0 20 23 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.12
Volume:	351.487
LogP:	1.687
LogD:	1.022
LogS:	-4.322
# Rotatable Bonds:	1
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	6.19
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.328
MDCK Permeability:	1.024710127239814e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.799
Human Intestinal Absorption (HIA):	0.255
20% Bioavailability (F20%):	0.492
30% Bioavailability (F30%):	0.827

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.754
Plasma Protein Binding (PPB):	90.19232940673828%
Volume Distribution (VD):	1.565
Pgp-substrate:	6.691781520843506%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.23
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.455
CYP3A4-inhibitor:	0.655
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	3.075
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.617
AMES Toxicity:	0.707
Rat Oral Acute Toxicity:	0.984
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.544
Carcinogencity:	0.061
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.475

Download Data

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

Natural Product: NPC472662

Natural Product ID:	NPC472662
*Common Name:**	BDBVWOALNBMPOM-IXNFLJKVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BDBVWOALNBMPOM-IXNFLJKVSA-N
Standard InCHI:	InChI=1S/C20H20O7/c1-18-15-13(27-17(18)22)5-10-11(6-12(24-2)9-3-4-25-14(9)10)19(15)7-20(23,16(18)21)26-8-19/h3-4,6,13,15-16,21,23H,5,7-8H2,1-2H3/t13-,15+,16-,18-,19+,20-/m1/s1
SMILES:	CC12C3C(CC4=C5C(=C(C=C4C36CC(C1O)(OC6)O)OC)C=CO5)OC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581405
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO33310	Icacina trichantha	Species	Icacinaceae	Eukaryota	Tuber	n.a.	n.a.	PMID[25782063]
NPO33310	Icacina trichantha	Species	Icacinaceae	Eukaryota	Tuber	n.a.	n.a.	PMID[26523419]
NPO33310	Icacina trichantha	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27340832]

☑ 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	3

Activity Type	# Activity
Cell Line	3

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[550353]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20000.0	nM	PMID[550353]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[550353]

☑ 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 NPC472662 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	406
0.1-0.2	1636
0.2-0.3	3129
0.3-0.4	7196
0.4-0.5	10881
0.5-0.6	5613
0.6-0.7	5805
0.7-0.8	7569
0.8-0.85	439
0.85-0.9	18
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472663
0.9357	High Similarity	NPC472661
0.9059	High Similarity	NPC255787
0.8941	High Similarity	NPC308156
0.8929	High Similarity	NPC472299
0.8895	High Similarity	NPC472660
0.8837	High Similarity	NPC291742
0.8807	High Similarity	NPC312630
0.8807	High Similarity	NPC324220
0.8757	High Similarity	NPC123153
0.8671	High Similarity	NPC41689
0.8655	High Similarity	NPC239270
0.8655	High Similarity	NPC303210
0.8655	High Similarity	NPC188649
0.8655	High Similarity	NPC95472
0.8636	High Similarity	NPC472620
0.8631	High Similarity	NPC44606
0.8629	High Similarity	NPC475641
0.8629	High Similarity	NPC475237
0.8621	High Similarity	NPC53640
0.8621	High Similarity	NPC296558
0.8613	High Similarity	NPC100849
0.8605	High Similarity	NPC288602
0.8605	High Similarity	NPC14822
0.8605	High Similarity	NPC283209
0.8605	High Similarity	NPC88841
0.8596	High Similarity	NPC218818
0.8588	High Similarity	NPC98776
0.858	High Similarity	NPC477670
0.858	High Similarity	NPC477572
0.858	High Similarity	NPC477571
0.858	High Similarity	NPC477573
0.8547	High Similarity	NPC470810
0.8547	High Similarity	NPC49009
0.8547	High Similarity	NPC169
0.8547	High Similarity	NPC18986
0.8539	High Similarity	NPC68381
0.8539	High Similarity	NPC294149
0.8531	High Similarity	NPC472584
0.8523	High Similarity	NPC294512
0.8523	High Similarity	NPC473202
0.8523	High Similarity	NPC472619
0.8508	High Similarity	NPC475656
0.8508	High Similarity	NPC475148
0.8506	High Similarity	NPC121995
0.8497	Intermediate Similarity	NPC285567
0.8492	Intermediate Similarity	NPC475233
0.8488	Intermediate Similarity	NPC470339
0.8483	Intermediate Similarity	NPC184624
0.848	Intermediate Similarity	NPC194499
0.848	Intermediate Similarity	NPC470625
0.8475	Intermediate Similarity	NPC315306
0.8475	Intermediate Similarity	NPC298778
0.8475	Intermediate Similarity	NPC131866
0.8475	Intermediate Similarity	NPC313717
0.8475	Intermediate Similarity	NPC120220
0.8466	Intermediate Similarity	NPC476459
0.8466	Intermediate Similarity	NPC472622
0.8457	Intermediate Similarity	NPC136641
0.8453	Intermediate Similarity	NPC475161
0.8453	Intermediate Similarity	NPC477860
0.8448	Intermediate Similarity	NPC56358
0.8439	Intermediate Similarity	NPC304839
0.8439	Intermediate Similarity	NPC79571
0.8439	Intermediate Similarity	NPC472055
0.8439	Intermediate Similarity	NPC220582
0.8436	Intermediate Similarity	NPC146803
0.8436	Intermediate Similarity	NPC300657
0.8436	Intermediate Similarity	NPC474345
0.8436	Intermediate Similarity	NPC224165
0.8436	Intermediate Similarity	NPC472665
0.843	Intermediate Similarity	NPC474611
0.843	Intermediate Similarity	NPC269495
0.843	Intermediate Similarity	NPC246647
0.843	Intermediate Similarity	NPC270044
0.843	Intermediate Similarity	NPC96342
0.843	Intermediate Similarity	NPC164110
0.843	Intermediate Similarity	NPC212967
0.8427	Intermediate Similarity	NPC307286
0.8427	Intermediate Similarity	NPC271385
0.8427	Intermediate Similarity	NPC111536
0.8427	Intermediate Similarity	NPC76128
0.8427	Intermediate Similarity	NPC30432
0.8427	Intermediate Similarity	NPC157522
0.8427	Intermediate Similarity	NPC5029
0.8409	Intermediate Similarity	NPC178851
0.8409	Intermediate Similarity	NPC472621
0.8409	Intermediate Similarity	NPC125465
0.8407	Intermediate Similarity	NPC228209
0.84	Intermediate Similarity	NPC86800
0.84	Intermediate Similarity	NPC471286
0.84	Intermediate Similarity	NPC91288
0.84	Intermediate Similarity	NPC472141
0.84	Intermediate Similarity	NPC205265
0.84	Intermediate Similarity	NPC472281
0.8398	Intermediate Similarity	NPC277710
0.8398	Intermediate Similarity	NPC153578
0.8398	Intermediate Similarity	NPC104682
0.8398	Intermediate Similarity	NPC114257
0.8398	Intermediate Similarity	NPC183843
0.8398	Intermediate Similarity	NPC299149
0.8393	Intermediate Similarity	NPC95526
0.8391	Intermediate Similarity	NPC92589
0.8391	Intermediate Similarity	NPC45124
0.8391	Intermediate Similarity	NPC269117
0.8391	Intermediate Similarity	NPC117985
0.8391	Intermediate Similarity	NPC74854
0.8391	Intermediate Similarity	NPC30655
0.8389	Intermediate Similarity	NPC475246
0.8389	Intermediate Similarity	NPC107244
0.8389	Intermediate Similarity	NPC478050
0.8389	Intermediate Similarity	NPC295914
0.8389	Intermediate Similarity	NPC325176
0.8389	Intermediate Similarity	NPC11062
0.8382	Intermediate Similarity	NPC287559
0.8382	Intermediate Similarity	NPC4950
0.8382	Intermediate Similarity	NPC40583
0.8382	Intermediate Similarity	NPC8389
0.838	Intermediate Similarity	NPC72455
0.838	Intermediate Similarity	NPC56953
0.838	Intermediate Similarity	NPC176413
0.838	Intermediate Similarity	NPC472054
0.8372	Intermediate Similarity	NPC88007
0.8372	Intermediate Similarity	NPC304692
0.8372	Intermediate Similarity	NPC477674
0.8372	Intermediate Similarity	NPC180924
0.8371	Intermediate Similarity	NPC51404
0.837	Intermediate Similarity	NPC105591
0.837	Intermediate Similarity	NPC240808
0.8362	Intermediate Similarity	NPC118086
0.8362	Intermediate Similarity	NPC320789
0.8362	Intermediate Similarity	NPC44602
0.8362	Intermediate Similarity	NPC473094
0.8353	Intermediate Similarity	NPC294511
0.8353	Intermediate Similarity	NPC121615
0.8352	Intermediate Similarity	NPC270312
0.8352	Intermediate Similarity	NPC472277
0.8352	Intermediate Similarity	NPC310572
0.8343	Intermediate Similarity	NPC35266
0.8343	Intermediate Similarity	NPC472664
0.8343	Intermediate Similarity	NPC5671
0.8343	Intermediate Similarity	NPC472298
0.8343	Intermediate Similarity	NPC276735
0.8333	Intermediate Similarity	NPC199533
0.8333	Intermediate Similarity	NPC68848
0.8333	Intermediate Similarity	NPC53917
0.8333	Intermediate Similarity	NPC3718
0.8333	Intermediate Similarity	NPC43971
0.8333	Intermediate Similarity	NPC19554
0.8333	Intermediate Similarity	NPC470454
0.8333	Intermediate Similarity	NPC74749
0.8333	Intermediate Similarity	NPC66804
0.8324	Intermediate Similarity	NPC114550
0.8324	Intermediate Similarity	NPC471920
0.8324	Intermediate Similarity	NPC129930
0.8324	Intermediate Similarity	NPC471922
0.8324	Intermediate Similarity	NPC140952
0.8324	Intermediate Similarity	NPC292712
0.8324	Intermediate Similarity	NPC312006
0.8324	Intermediate Similarity	NPC471921
0.8324	Intermediate Similarity	NPC475967
0.8324	Intermediate Similarity	NPC474075
0.8324	Intermediate Similarity	NPC20114
0.8324	Intermediate Similarity	NPC158542
0.8315	Intermediate Similarity	NPC41853
0.8315	Intermediate Similarity	NPC473096
0.8315	Intermediate Similarity	NPC222455
0.8315	Intermediate Similarity	NPC473095
0.8315	Intermediate Similarity	NPC259905
0.8314	Intermediate Similarity	NPC477671
0.8314	Intermediate Similarity	NPC477687
0.8314	Intermediate Similarity	NPC104736
0.8314	Intermediate Similarity	NPC148938
0.8306	Intermediate Similarity	NPC8927
0.8306	Intermediate Similarity	NPC240508
0.8306	Intermediate Similarity	NPC478001
0.8305	Intermediate Similarity	NPC472452
0.8305	Intermediate Similarity	NPC119589
0.8304	Intermediate Similarity	NPC10429
0.8297	Intermediate Similarity	NPC212290
0.8295	Intermediate Similarity	NPC476295
0.8295	Intermediate Similarity	NPC18100
0.8287	Intermediate Similarity	NPC46958
0.8287	Intermediate Similarity	NPC196771
0.8286	Intermediate Similarity	NPC15212
0.8284	Intermediate Similarity	NPC195325
0.8276	Intermediate Similarity	NPC239118
0.8276	Intermediate Similarity	NPC476350
0.8276	Intermediate Similarity	NPC472877
0.8276	Intermediate Similarity	NPC50430
0.8276	Intermediate Similarity	NPC476349
0.827	Intermediate Similarity	NPC73703
0.8268	Intermediate Similarity	NPC241874
0.8266	Intermediate Similarity	NPC81405
0.8266	Intermediate Similarity	NPC472776
0.8266	Intermediate Similarity	NPC477675
0.8266	Intermediate Similarity	NPC472778
0.8266	Intermediate Similarity	NPC299038
0.8266	Intermediate Similarity	NPC7059
0.8266	Intermediate Similarity	NPC472777

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 NPC472662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	870
0.2-0.3	1891
0.3-0.4	2664
0.4-0.5	2038
0.5-0.6	875
0.6-0.7	319
0.7-0.8	136
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8588	High Similarity	NPD6559	Discontinued
0.8212	Intermediate Similarity	NPD5844	Phase 1
0.8202	Intermediate Similarity	NPD7473	Discontinued
0.815	Intermediate Similarity	NPD7819	Suspended
0.8136	Intermediate Similarity	NPD6232	Discontinued
0.8118	Intermediate Similarity	NPD920	Approved
0.8081	Intermediate Similarity	NPD6599	Discontinued
0.8056	Intermediate Similarity	NPD3818	Discontinued
0.8054	Intermediate Similarity	NPD8434	Phase 2
0.8046	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD5494	Approved
0.7989	Intermediate Similarity	NPD6801	Discontinued
0.7978	Intermediate Similarity	NPD6959	Discontinued
0.7966	Intermediate Similarity	NPD919	Approved
0.7955	Intermediate Similarity	NPD4967	Phase 2
0.7955	Intermediate Similarity	NPD4966	Approved
0.7955	Intermediate Similarity	NPD4965	Approved
0.7943	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD3749	Approved
0.791	Intermediate Similarity	NPD7075	Discontinued
0.7895	Intermediate Similarity	NPD2534	Approved
0.7895	Intermediate Similarity	NPD2532	Approved
0.7895	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7199	Phase 2
0.7865	Intermediate Similarity	NPD6234	Discontinued
0.7809	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD3817	Phase 2
0.7796	Intermediate Similarity	NPD8312	Approved
0.7796	Intermediate Similarity	NPD8313	Approved
0.7789	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD37	Approved
0.7784	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1247	Approved
0.7771	Intermediate Similarity	NPD4380	Phase 2
0.7765	Intermediate Similarity	NPD4628	Phase 3
0.7753	Intermediate Similarity	NPD3882	Suspended
0.7753	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6799	Approved
0.7727	Intermediate Similarity	NPD7411	Suspended
0.7714	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7074	Phase 3
0.7663	Intermediate Similarity	NPD7228	Approved
0.765	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD6166	Phase 2
0.765	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5761	Phase 2
0.764	Intermediate Similarity	NPD2801	Approved
0.764	Intermediate Similarity	NPD5760	Phase 2
0.7622	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7054	Approved
0.7602	Intermediate Similarity	NPD1243	Approved
0.7598	Intermediate Similarity	NPD5402	Approved
0.7598	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD2346	Discontinued
0.7586	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7472	Approved
0.7569	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3751	Discontinued
0.7562	Intermediate Similarity	NPD8151	Discontinued
0.7556	Intermediate Similarity	NPD7768	Phase 2
0.7554	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD1465	Phase 2
0.7541	Intermediate Similarity	NPD3787	Discontinued
0.7541	Intermediate Similarity	NPD7229	Phase 3
0.754	Intermediate Similarity	NPD6797	Phase 2
0.7529	Intermediate Similarity	NPD2796	Approved
0.7526	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD2800	Approved
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7808	Phase 3
0.7447	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6273	Approved
0.7442	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1549	Phase 2
0.7429	Intermediate Similarity	NPD1511	Approved
0.7427	Intermediate Similarity	NPD1551	Phase 2
0.7401	Intermediate Similarity	NPD5403	Approved
0.74	Intermediate Similarity	NPD7435	Discontinued
0.7399	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8150	Discontinued
0.7386	Intermediate Similarity	NPD5401	Approved
0.7386	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2799	Discontinued
0.7356	Intermediate Similarity	NPD3750	Approved
0.7351	Intermediate Similarity	NPD5711	Approved
0.7351	Intermediate Similarity	NPD5710	Approved
0.7345	Intermediate Similarity	NPD1512	Approved
0.7337	Intermediate Similarity	NPD6782	Approved
0.7337	Intermediate Similarity	NPD6781	Approved
0.7337	Intermediate Similarity	NPD6778	Approved
0.7337	Intermediate Similarity	NPD6777	Approved
0.7337	Intermediate Similarity	NPD6780	Approved
0.7337	Intermediate Similarity	NPD6776	Approved
0.7337	Intermediate Similarity	NPD6779	Approved
0.7317	Intermediate Similarity	NPD7783	Phase 2
0.7317	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD6765	Approved
0.7316	Intermediate Similarity	NPD6764	Approved
0.7287	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3748	Approved
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.7257	Intermediate Similarity	NPD7003	Approved
0.7257	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1607	Approved
0.7232	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2935	Discontinued
0.7225	Intermediate Similarity	NPD8404	Phase 2
0.7204	Intermediate Similarity	NPD8127	Discontinued
0.7184	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7874	Approved
0.7184	Intermediate Similarity	NPD2344	Approved
0.7165	Intermediate Similarity	NPD6785	Approved
0.7165	Intermediate Similarity	NPD6784	Approved
0.7159	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7286	Phase 2
0.7158	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD7680	Approved
0.7143	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD7697	Approved
0.7135	Intermediate Similarity	NPD7390	Discontinued
0.7135	Intermediate Similarity	NPD1240	Approved
0.7126	Intermediate Similarity	NPD6099	Approved
0.7126	Intermediate Similarity	NPD6100	Approved
0.7118	Intermediate Similarity	NPD2313	Discontinued
0.7118	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8320	Phase 1
0.7108	Intermediate Similarity	NPD7870	Phase 2
0.7108	Intermediate Similarity	NPD8319	Approved
0.7108	Intermediate Similarity	NPD7871	Phase 2
0.7098	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6823	Phase 2
0.7087	Intermediate Similarity	NPD7701	Phase 2
0.7085	Intermediate Similarity	NPD6535	Approved
0.7085	Intermediate Similarity	NPD6534	Approved
0.7083	Intermediate Similarity	NPD5953	Discontinued
0.7067	Intermediate Similarity	NPD7801	Approved
0.7056	Intermediate Similarity	NPD4287	Approved
0.7029	Intermediate Similarity	NPD5405	Approved
0.7029	Intermediate Similarity	NPD5408	Approved
0.7029	Intermediate Similarity	NPD5406	Approved
0.7029	Intermediate Similarity	NPD5404	Approved
0.7026	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2309	Approved
0.7018	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7177	Discontinued
0.7015	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1471	Phase 3
0.698	Remote Similarity	NPD7699	Phase 2
0.698	Remote Similarity	NPD7700	Phase 2
0.6967	Remote Similarity	NPD7930	Approved
0.6959	Remote Similarity	NPD7685	Pre-registration
0.6959	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6651	Approved
0.6946	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2438	Suspended
0.6927	Remote Similarity	NPD5005	Approved
0.6927	Remote Similarity	NPD5006	Approved
0.6927	Remote Similarity	NPD7799	Discontinued
0.6916	Remote Similarity	NPD4111	Phase 1
0.6916	Remote Similarity	NPD4665	Approved
0.6912	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6674	Discontinued
0.6897	Remote Similarity	NPD230	Phase 1
0.6897	Remote Similarity	NPD1933	Approved
0.6897	Remote Similarity	NPD447	Suspended
0.6897	Remote Similarity	NPD6355	Discontinued
0.6895	Remote Similarity	NPD6808	Phase 2
0.6882	Remote Similarity	NPD2798	Approved
0.6875	Remote Similarity	NPD7033	Discontinued
0.6866	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6212	Phase 3
0.6866	Remote Similarity	NPD6213	Phase 3
0.6865	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1283	Approved
0.6863	Remote Similarity	NPD8285	Discontinued
0.6852	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3057	Approved
0.6839	Remote Similarity	NPD943	Approved
0.6839	Remote Similarity	NPD4060	Phase 1
0.6839	Remote Similarity	NPD2979	Phase 3
0.6839	Remote Similarity	NPD4140	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