NPASS Compound

Structure

CID316691 OpenBabel06191716132D 26 29 0 0 1 0 0 0 0 0999 V2000 4.8597 0.1267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4669 -0.6785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9295 -2.5376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8048 0.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8044 -0.4648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9278 1.8577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1237 1.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4660 0.9303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5371 0.9298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1981 -1.2682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8043 0.4648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3935 -0.8040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9309 0.1261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3937 -1.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 0.9290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8046 -0.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7332 -0.4641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0002 -0.9290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7325 1.3937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1242 0.4640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7330 0.4649 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9288 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0007 1.8578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5366 1.8586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6800 -0.0009 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 5 2 0 0 0 0 4 15 1 0 0 0 0 5 18 1 0 0 0 0 6 7 2 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 21 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 21 1 1 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 24 2 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 21 22 1 1 0 0 0 22 12 1 1 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.15
Volume:	368.912
LogP:	3.801
LogD:	3.1
LogS:	-4.264
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.819
Synthetic Accessibility Score:	5.215
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.704
MDCK Permeability:	2.172552740375977e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.206
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.617
Plasma Protein Binding (PPB):	88.00607299804688%
Volume Distribution (VD):	2.103
Pgp-substrate:	8.677207946777344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.614
CYP1A2-substrate:	0.566
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.772
CYP2C9-inhibitor:	0.56
CYP2C9-substrate:	0.532
CYP2D6-inhibitor:	0.278
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.495
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	11.794
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.163
Human Hepatotoxicity (H-HT):	0.871
Drug-inuced Liver Injury (DILI):	0.41
AMES Toxicity:	0.715
Rat Oral Acute Toxicity:	0.914
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.575
Carcinogencity:	0.884
Eye Corrosion:	0.003
Eye Irritation:	0.099
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC316691

Natural Product ID:	NPC316691
*Common Name:**	Ehretianone
IUPAC Name:	n.a.
Synonyms:	Ehretianone
Standard InCHIKey:	HBDVLYQTRSOPRO-BULFRSBZSA-N
Standard InCHI:	InChI=1S/C22H22O4/c1-13(2)8-9-21-17-10-14(3)12-22(21,20(25)7-6-19(21)24)26-18-5-4-15(23)11-16(17)18/h4-8,10-11,17,23H,9,12H2,1-3H3/t17-,21-,22+/m0/s1
SMILES:	CC(=CC[C@@]12C(=O)C=CC(=O)[C@@]32CC(=C[C@H]1c1cc(O)ccc1O3)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518366
PubChem CID:	10405602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO30649	Ehretia buxifolia	Species	Ehretiaceae	Eukaryota	n.a.	root	n.a.	PMID[8759162]

☑ 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	7

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Activity	=	43.3	%	PMID[517930]
NPT2	Others	Unspecified	Activity	=	26.7	%	PMID[517930]
NPT2	Others	Unspecified	Activity	=	13.3	%	PMID[517930]
NPT2	Others	Unspecified	Activity	=	16.7	%	PMID[517930]
NPT2	Others	Unspecified	Activity	=	21.7	%	PMID[517930]
NPT2	Others	Unspecified	Activity	=	38.3	%	PMID[517930]
NPT2	Others	Unspecified	Activity	=	45.0	%	PMID[517930]

☑ 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 NPC316691 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	385
0.1-0.2	1518
0.2-0.3	3541
0.3-0.4	8610
0.4-0.5	10229
0.5-0.6	4773
0.6-0.7	9570
0.7-0.8	4007
0.8-0.85	60
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9927	High Similarity	NPC471600
0.8531	High Similarity	NPC474610
0.8489	Intermediate Similarity	NPC201419
0.8408	Intermediate Similarity	NPC475106
0.8403	Intermediate Similarity	NPC21797
0.8403	Intermediate Similarity	NPC194847
0.8392	Intermediate Similarity	NPC477210
0.838	Intermediate Similarity	NPC118253
0.8369	Intermediate Similarity	NPC196621
0.8356	Intermediate Similarity	NPC79372
0.8345	Intermediate Similarity	NPC301341
0.8344	Intermediate Similarity	NPC476929
0.8333	Intermediate Similarity	NPC22222
0.8333	Intermediate Similarity	NPC281513
0.831	Intermediate Similarity	NPC474143
0.831	Intermediate Similarity	NPC474246
0.8255	Intermediate Similarity	NPC474599
0.8252	Intermediate Similarity	NPC251549
0.8239	Intermediate Similarity	NPC475880
0.8239	Intermediate Similarity	NPC476931
0.8231	Intermediate Similarity	NPC76312
0.8231	Intermediate Similarity	NPC477408
0.8224	Intermediate Similarity	NPC474556
0.8219	Intermediate Similarity	NPC284184
0.8219	Intermediate Similarity	NPC98804
0.8201	Intermediate Similarity	NPC248557
0.82	Intermediate Similarity	NPC477409
0.8194	Intermediate Similarity	NPC171968
0.8182	Intermediate Similarity	NPC141549
0.8169	Intermediate Similarity	NPC271832
0.8169	Intermediate Similarity	NPC59654
0.8163	Intermediate Similarity	NPC475104
0.8163	Intermediate Similarity	NPC265335
0.8162	Intermediate Similarity	NPC51341
0.8153	Intermediate Similarity	NPC67197
0.8138	Intermediate Similarity	NPC27394
0.8137	Intermediate Similarity	NPC476056
0.8125	Intermediate Similarity	NPC312560
0.8117	Intermediate Similarity	NPC475718
0.8112	Intermediate Similarity	NPC278787
0.8095	Intermediate Similarity	NPC477534
0.8089	Intermediate Similarity	NPC469507
0.8086	Intermediate Similarity	NPC193222
0.8082	Intermediate Similarity	NPC22644
0.8067	Intermediate Similarity	NPC201297
0.8067	Intermediate Similarity	NPC474154
0.8065	Intermediate Similarity	NPC305965
0.8056	Intermediate Similarity	NPC205360
0.8054	Intermediate Similarity	NPC475044
0.8054	Intermediate Similarity	NPC475063
0.805	Intermediate Similarity	NPC43490
0.805	Intermediate Similarity	NPC475107
0.8042	Intermediate Similarity	NPC206028
0.8039	Intermediate Similarity	NPC252208
0.8037	Intermediate Similarity	NPC286074
0.8037	Intermediate Similarity	NPC54903
0.8028	Intermediate Similarity	NPC477212
0.8028	Intermediate Similarity	NPC477211
0.8028	Intermediate Similarity	NPC477214
0.8028	Intermediate Similarity	NPC95034
0.8028	Intermediate Similarity	NPC142087
0.8028	Intermediate Similarity	NPC319422
0.8027	Intermediate Similarity	NPC471670
0.8027	Intermediate Similarity	NPC475549
0.8025	Intermediate Similarity	NPC3898
0.8025	Intermediate Similarity	NPC62444
0.8013	Intermediate Similarity	NPC142527
0.8012	Intermediate Similarity	NPC469395
0.8	Intermediate Similarity	NPC61382
0.8	Intermediate Similarity	NPC101957
0.8	Intermediate Similarity	NPC120105
0.8	Intermediate Similarity	NPC103816
0.7987	Intermediate Similarity	NPC37135
0.7987	Intermediate Similarity	NPC475045
0.7987	Intermediate Similarity	NPC186397
0.7987	Intermediate Similarity	NPC470407
0.7987	Intermediate Similarity	NPC475012
0.7986	Intermediate Similarity	NPC253488
0.7986	Intermediate Similarity	NPC7569
0.7975	Intermediate Similarity	NPC470352
0.7975	Intermediate Similarity	NPC470354
0.7974	Intermediate Similarity	NPC329678
0.7973	Intermediate Similarity	NPC156888
0.7973	Intermediate Similarity	NPC470721
0.7973	Intermediate Similarity	NPC6100
0.7973	Intermediate Similarity	NPC470722
0.7973	Intermediate Similarity	NPC118366
0.7973	Intermediate Similarity	NPC471542
0.7972	Intermediate Similarity	NPC47288
0.7963	Intermediate Similarity	NPC316262
0.7963	Intermediate Similarity	NPC314653
0.7962	Intermediate Similarity	NPC280530
0.7962	Intermediate Similarity	NPC178964
0.7962	Intermediate Similarity	NPC95842
0.7961	Intermediate Similarity	NPC89664
0.7961	Intermediate Similarity	NPC274085
0.7961	Intermediate Similarity	NPC169942
0.7961	Intermediate Similarity	NPC473813
0.7961	Intermediate Similarity	NPC473812
0.795	Intermediate Similarity	NPC94796
0.7949	Intermediate Similarity	NPC81474
0.7947	Intermediate Similarity	NPC329493
0.7945	Intermediate Similarity	NPC470871
0.7943	Intermediate Similarity	NPC474237
0.7943	Intermediate Similarity	NPC147896
0.7937	Intermediate Similarity	NPC313368
0.7937	Intermediate Similarity	NPC472618
0.7935	Intermediate Similarity	NPC266499
0.7935	Intermediate Similarity	NPC223988
0.7931	Intermediate Similarity	NPC258073
0.7929	Intermediate Similarity	NPC49441
0.7925	Intermediate Similarity	NPC196448
0.7925	Intermediate Similarity	NPC201127
0.7919	Intermediate Similarity	NPC475028
0.7919	Intermediate Similarity	NPC474943
0.7919	Intermediate Similarity	NPC476025
0.7919	Intermediate Similarity	NPC173980
0.7919	Intermediate Similarity	NPC475005
0.7914	Intermediate Similarity	NPC120857
0.7914	Intermediate Similarity	NPC85047
0.7914	Intermediate Similarity	NPC17274
0.7911	Intermediate Similarity	NPC478159
0.7911	Intermediate Similarity	NPC275575
0.7911	Intermediate Similarity	NPC478161
0.7911	Intermediate Similarity	NPC326910
0.7908	Intermediate Similarity	NPC472446
0.7908	Intermediate Similarity	NPC470673
0.7908	Intermediate Similarity	NPC117716
0.7908	Intermediate Similarity	NPC470674
0.7908	Intermediate Similarity	NPC474630
0.7908	Intermediate Similarity	NPC472447
0.7905	Intermediate Similarity	NPC232996
0.7899	Intermediate Similarity	NPC471449
0.7898	Intermediate Similarity	NPC45934
0.7898	Intermediate Similarity	NPC470353
0.7895	Intermediate Similarity	NPC1534
0.7895	Intermediate Similarity	NPC204469
0.7892	Intermediate Similarity	NPC475080
0.7892	Intermediate Similarity	NPC469393
0.7888	Intermediate Similarity	NPC472275
0.7887	Intermediate Similarity	NPC224657
0.7887	Intermediate Similarity	NPC477213
0.7885	Intermediate Similarity	NPC227122
0.7881	Intermediate Similarity	NPC124365
0.7875	Intermediate Similarity	NPC185258
0.7875	Intermediate Similarity	NPC172770
0.7872	Intermediate Similarity	NPC135062
0.7871	Intermediate Similarity	NPC474107
0.7871	Intermediate Similarity	NPC296869
0.7867	Intermediate Similarity	NPC476191
0.7862	Intermediate Similarity	NPC471968
0.7862	Intermediate Similarity	NPC470725
0.7862	Intermediate Similarity	NPC164244
0.7857	Intermediate Similarity	NPC470676
0.7857	Intermediate Similarity	NPC473132
0.7857	Intermediate Similarity	NPC196114
0.7857	Intermediate Similarity	NPC211565
0.7857	Intermediate Similarity	NPC473135
0.7857	Intermediate Similarity	NPC477955
0.7848	Intermediate Similarity	NPC305710
0.7847	Intermediate Similarity	NPC237225
0.7847	Intermediate Similarity	NPC176590
0.7843	Intermediate Similarity	NPC475813
0.784	Intermediate Similarity	NPC473022
0.7834	Intermediate Similarity	NPC470675
0.7834	Intermediate Similarity	NPC473131
0.7832	Intermediate Similarity	NPC306765
0.7831	Intermediate Similarity	NPC118128
0.7829	Intermediate Similarity	NPC69755
0.7826	Intermediate Similarity	NPC284495
0.7823	Intermediate Similarity	NPC477536
0.7823	Intermediate Similarity	NPC211352
0.7821	Intermediate Similarity	NPC226578
0.7821	Intermediate Similarity	NPC471114
0.7821	Intermediate Similarity	NPC269420
0.7818	Intermediate Similarity	NPC20734
0.7817	Intermediate Similarity	NPC190086
0.7817	Intermediate Similarity	NPC276962
0.7815	Intermediate Similarity	NPC477537
0.7812	Intermediate Similarity	NPC476930
0.7812	Intermediate Similarity	NPC272196
0.7812	Intermediate Similarity	NPC282390
0.7812	Intermediate Similarity	NPC79053
0.7812	Intermediate Similarity	NPC281137
0.7808	Intermediate Similarity	NPC153019
0.7808	Intermediate Similarity	NPC324488
0.7806	Intermediate Similarity	NPC478163
0.7806	Intermediate Similarity	NPC166757
0.7806	Intermediate Similarity	NPC14001
0.7805	Intermediate Similarity	NPC251336
0.7805	Intermediate Similarity	NPC476255
0.7799	Intermediate Similarity	NPC55662
0.7799	Intermediate Similarity	NPC471116
0.7799	Intermediate Similarity	NPC166054
0.7792	Intermediate Similarity	NPC326500
0.7792	Intermediate Similarity	NPC478019
0.7792	Intermediate Similarity	NPC473951
0.7791	Intermediate Similarity	NPC159508
0.7791	Intermediate Similarity	NPC306321
0.7791	Intermediate Similarity	NPC303460

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 NPC316691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	950
0.2-0.3	1563
0.3-0.4	2621
0.4-0.5	2033
0.5-0.6	1096
0.6-0.7	454
0.7-0.8	78
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8121	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD6100	Approved
0.7973	Intermediate Similarity	NPD6099	Approved
0.78	Intermediate Similarity	NPD2346	Discontinued
0.7737	Intermediate Similarity	NPD6671	Approved
0.7677	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3268	Approved
0.7616	Intermediate Similarity	NPD2935	Discontinued
0.7595	Intermediate Similarity	NPD3226	Approved
0.7566	Intermediate Similarity	NPD2344	Approved
0.755	Intermediate Similarity	NPD2799	Discontinued
0.7517	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD2313	Discontinued
0.7466	Intermediate Similarity	NPD2798	Approved
0.7452	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1471	Phase 3
0.744	Intermediate Similarity	NPD3751	Discontinued
0.7436	Intermediate Similarity	NPD3300	Phase 2
0.7432	Intermediate Similarity	NPD7095	Approved
0.7413	Intermediate Similarity	NPD3496	Discontinued
0.7407	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4749	Approved
0.7378	Intermediate Similarity	NPD7075	Discontinued
0.7372	Intermediate Similarity	NPD2309	Approved
0.7362	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2800	Approved
0.7329	Intermediate Similarity	NPD6599	Discontinued
0.7329	Intermediate Similarity	NPD6696	Suspended
0.731	Intermediate Similarity	NPD1608	Approved
0.7305	Intermediate Similarity	NPD7340	Approved
0.7301	Intermediate Similarity	NPD2801	Approved
0.7301	Intermediate Similarity	NPD7819	Suspended
0.7301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1512	Approved
0.729	Intermediate Similarity	NPD1549	Phase 2
0.7289	Intermediate Similarity	NPD5494	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7279	Intermediate Similarity	NPD3267	Approved
0.7279	Intermediate Similarity	NPD3266	Approved
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8434	Phase 2
0.7256	Intermediate Similarity	NPD5402	Approved
0.7246	Intermediate Similarity	NPD6959	Discontinued
0.7244	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6844	Discontinued
0.7239	Intermediate Similarity	NPD1934	Approved
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2932	Approved
0.7222	Intermediate Similarity	NPD1778	Approved
0.7222	Intermediate Similarity	NPD4380	Phase 2
0.7219	Intermediate Similarity	NPD8032	Phase 2
0.7219	Intermediate Similarity	NPD6166	Phase 2
0.7219	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1398	Phase 1
0.7212	Intermediate Similarity	NPD3882	Suspended
0.7208	Intermediate Similarity	NPD4308	Phase 3
0.7197	Intermediate Similarity	NPD7003	Approved
0.7197	Intermediate Similarity	NPD8166	Discontinued
0.7197	Intermediate Similarity	NPD4628	Phase 3
0.7197	Intermediate Similarity	NPD3750	Approved
0.7192	Intermediate Similarity	NPD9717	Approved
0.7192	Intermediate Similarity	NPD3972	Approved
0.7188	Intermediate Similarity	NPD6273	Approved
0.7184	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2861	Phase 2
0.7178	Intermediate Similarity	NPD7411	Suspended
0.717	Intermediate Similarity	NPD1511	Approved
0.7162	Intermediate Similarity	NPD1203	Approved
0.7162	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD411	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7124	Intermediate Similarity	NPD447	Suspended
0.7117	Intermediate Similarity	NPD7028	Phase 2
0.7115	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7103	Intermediate Similarity	NPD3019	Approved
0.7103	Intermediate Similarity	NPD17	Approved
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7097	Intermediate Similarity	NPD1510	Phase 2
0.7093	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5844	Phase 1
0.7092	Intermediate Similarity	NPD1241	Discontinued
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7078	Intermediate Similarity	NPD1607	Approved
0.707	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3749	Approved
0.7063	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6799	Approved
0.7062	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD1240	Approved
0.7051	Intermediate Similarity	NPD2796	Approved
0.7048	Intermediate Similarity	NPD3817	Phase 2
0.7034	Intermediate Similarity	NPD5585	Approved
0.703	Intermediate Similarity	NPD6801	Discontinued
0.7029	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6797	Phase 2
0.7007	Intermediate Similarity	NPD1535	Discovery
0.7007	Intermediate Similarity	NPD1611	Approved
0.7007	Intermediate Similarity	NPD1201	Approved
0.7006	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7236	Approved
0.6994	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4626	Approved
0.698	Remote Similarity	NPD3225	Approved
0.6977	Remote Similarity	NPD7473	Discontinued
0.6971	Remote Similarity	NPD7251	Discontinued
0.6968	Remote Similarity	NPD6651	Approved
0.6959	Remote Similarity	NPD1481	Phase 2
0.6948	Remote Similarity	NPD4307	Phase 2
0.6941	Remote Similarity	NPD8127	Discontinued
0.6937	Remote Similarity	NPD2354	Approved
0.6933	Remote Similarity	NPD5403	Approved
0.6932	Remote Similarity	NPD7808	Phase 3
0.6928	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7985	Registered
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7097	Phase 1
0.6923	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6782	Approved
0.6919	Remote Similarity	NPD6780	Approved
0.6919	Remote Similarity	NPD6781	Approved
0.6919	Remote Similarity	NPD6779	Approved
0.6919	Remote Similarity	NPD6778	Approved
0.6919	Remote Similarity	NPD6776	Approved
0.6919	Remote Similarity	NPD6777	Approved
0.6918	Remote Similarity	NPD1651	Approved
0.6918	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2533	Approved
0.6914	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD2534	Approved
0.6908	Remote Similarity	NPD6832	Phase 2
0.6908	Remote Similarity	NPD4908	Phase 1
0.6905	Remote Similarity	NPD7768	Phase 2
0.6905	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6232	Discontinued
0.6899	Remote Similarity	NPD5763	Approved
0.6899	Remote Similarity	NPD5762	Approved
0.6898	Remote Similarity	NPD7435	Discontinued
0.6897	Remote Similarity	NPD7644	Approved
0.6893	Remote Similarity	NPD8312	Approved
0.6893	Remote Similarity	NPD8313	Approved
0.6889	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5761	Phase 2
0.6886	Remote Similarity	NPD5760	Phase 2
0.6879	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3748	Approved
0.6879	Remote Similarity	NPD3446	Phase 1
0.6875	Remote Similarity	NPD6765	Approved
0.6875	Remote Similarity	NPD6764	Approved
0.6875	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4110	Phase 3
0.6871	Remote Similarity	NPD5049	Phase 3
0.6867	Remote Similarity	NPD1283	Approved
0.6857	Remote Similarity	NPD7074	Phase 3
0.6855	Remote Similarity	NPD2424	Discontinued
0.6845	Remote Similarity	NPD2296	Approved
0.6842	Remote Similarity	NPD1247	Approved
0.6839	Remote Similarity	NPD4140	Approved
0.6838	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1551	Phase 2
0.6826	Remote Similarity	NPD7577	Discontinued
0.6818	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5401	Approved
0.6809	Remote Similarity	NPD7697	Approved
0.6809	Remote Similarity	NPD7698	Approved
0.6809	Remote Similarity	NPD7696	Phase 3
0.6803	Remote Similarity	NPD5691	Approved
0.68	Remote Similarity	NPD4359	Approved
0.68	Remote Similarity	NPD7054	Approved
0.68	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6004	Phase 3
0.6792	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2353	Approved
0.6792	Remote Similarity	NPD6005	Phase 3
0.6792	Remote Similarity	NPD6002	Phase 3
0.6792	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7239	Suspended
0.678	Remote Similarity	NPD6559	Discontinued
0.6776	Remote Similarity	NPD5647	Approved
0.6776	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7870	Phase 2
0.6772	Remote Similarity	NPD7871	Phase 2
0.677	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7472	Approved
0.6758	Remote Similarity	NPD2490	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