NPASS Compound

Structure

NPC469889 OpenBabel07101718182D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.0976 3.3957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1254 -0.5387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4052 -3.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4271 -3.7192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6723 0.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4155 0.8213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7142 -4.8782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1399 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 -2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5134 1.4394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1180 -2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.2076 1.7995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2565 2.1085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6924 -5.0861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9507 2.4686 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -4.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0486 3.0866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1473 -0.3308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 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 32 1 0 0 0 0 2 33 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 16 1 0 0 0 0 5 8 1 0 0 0 0 5 17 2 0 0 0 0 6 9 2 0 0 0 0 6 17 1 0 0 0 0 7 10 2 0 0 0 0 7 18 1 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 28 2 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 24 2 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 15 34 1 0 0 0 0 17 27 1 0 0 0 0 18 25 1 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 30 1 0 0 0 0 23 32 1 0 0 0 0 24 26 1 0 0 0 0 24 33 1 0 0 0 0 25 35 1 0 0 0 0 26 35 1 0 0 0 0 27 31 2 0 0 0 0 27 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.15
Volume:	480.007
LogP:	3.617
LogD:	3.238
LogS:	-3.565
# Rotatable Bonds:	9
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	3.529
Fsp3:	0.185
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.924
MDCK Permeability:	1.0243614269711543e-05
Pgp-inhibitor:	0.301
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	100.041015625%
Volume Distribution (VD):	0.409
Pgp-substrate:	1.829384684562683%

ADMET: Metabolism

CYP1A2-inhibitor:	0.222
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.886
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.397
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.779
CYP3A4-substrate:	0.661

ADMET: Excretion

Clearance (CL):	4.688
Half-life (T1/2):	0.697

ADMET: Toxicity

hERG Blockers:	0.161
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.297
AMES Toxicity:	0.213
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.705
Skin Sensitization:	0.915
Carcinogencity:	0.724
Eye Corrosion:	0.003
Eye Irritation:	0.487
Respiratory Toxicity:	0.147

Download Data

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

Natural Product: NPC469889

Natural Product ID:	NPC469889
*Common Name:**	2,3-Dihydro-2-(4'-Hydroxy-3'-Methoxyphenyl)-3-P-Hydroxybenzoyloxymethyl-5-(2-Formylvinyl)-7-Methoxybenzofuran
IUPAC Name:	[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-[(E)-3-oxoprop-1-enyl]-2,3-dihydro-1-benzofuran-3-yl]methyl 4-hydroxybenzoate
Synonyms:
Standard InCHIKey:	JRDSHOZYAFZUGI-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C27H24O8/c1-32-23-14-18(7-10-22(23)30)25-21(15-34-27(31)17-5-8-19(29)9-6-17)20-12-16(4-3-11-28)13-24(33-2)26(20)35-25/h3-14,21,25,29-30H,15H2,1-2H3/b4-3+
SMILES:	COC1=CC(=CC2=C1OC(C2COC(=O)C3=CC=C(C=C3)O)C4=CC(=C(C=C4)O)OC)C=CC=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224885
PubChem CID:	49866360
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO32697	calamus quiquesetinervius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20056545]
NPO32697	calamus quiquesetinervius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20825224]

☑ 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	3
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[493241]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	69000.0	nM	PMID[493241]
NPT1	Others	Radical scavenging activity		IC50	>	100000.0	nM	PMID[493241]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19100.0	nM	PMID[493241]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[493241]

☑ 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 NPC469889 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	360
0.1-0.2	1404
0.2-0.3	3130
0.3-0.4	7652
0.4-0.5	10661
0.5-0.6	3753
0.6-0.7	4899
0.7-0.8	8567
0.8-0.85	1952
0.85-0.9	290
0.9-0.95	24
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC45943
0.9487	High Similarity	NPC216916
0.9474	High Similarity	NPC267091
0.9416	High Similarity	NPC180901
0.9416	High Similarity	NPC300757
0.9412	High Similarity	NPC131121
0.9408	High Similarity	NPC243891
0.9371	High Similarity	NPC43065
0.9317	High Similarity	NPC180768
0.9211	High Similarity	NPC236166
0.9202	High Similarity	NPC316539
0.9125	High Similarity	NPC272750
0.9125	High Similarity	NPC223006
0.9125	High Similarity	NPC134047
0.9125	High Similarity	NPC173729
0.9062	High Similarity	NPC144557
0.9057	High Similarity	NPC472961
0.9057	High Similarity	NPC472962
0.9057	High Similarity	NPC53889
0.8994	High Similarity	NPC87317
0.8981	High Similarity	NPC469888
0.8961	High Similarity	NPC472969
0.8931	High Similarity	NPC114179
0.8931	High Similarity	NPC156818
0.8931	High Similarity	NPC160512
0.8931	High Similarity	NPC68324
0.8931	High Similarity	NPC289322
0.8931	High Similarity	NPC143328
0.8931	High Similarity	NPC38779
0.8917	High Similarity	NPC115203
0.8903	High Similarity	NPC98809
0.8903	High Similarity	NPC476394
0.8889	High Similarity	NPC163898
0.8882	High Similarity	NPC92589
0.8868	High Similarity	NPC88803
0.8868	High Similarity	NPC300845
0.8868	High Similarity	NPC250436
0.8868	High Similarity	NPC104983
0.8868	High Similarity	NPC165483
0.8868	High Similarity	NPC291948
0.8854	High Similarity	NPC476434
0.8848	High Similarity	NPC131866
0.8848	High Similarity	NPC102277
0.8848	High Similarity	NPC279209
0.8831	High Similarity	NPC287495
0.8831	High Similarity	NPC9370
0.8827	High Similarity	NPC476372
0.8827	High Similarity	NPC476371
0.8824	High Similarity	NPC284881
0.8824	High Similarity	NPC93433
0.8824	High Similarity	NPC474444
0.8824	High Similarity	NPC264706
0.882	High Similarity	NPC292415
0.882	High Similarity	NPC24164
0.8816	High Similarity	NPC67467
0.8816	High Similarity	NPC131971
0.8812	High Similarity	NPC35598
0.8812	High Similarity	NPC222689
0.8797	High Similarity	NPC474656
0.8797	High Similarity	NPC470769
0.8795	High Similarity	NPC247964
0.8788	High Similarity	NPC41494
0.8788	High Similarity	NPC186100
0.8788	High Similarity	NPC216403
0.878	High Similarity	NPC472452
0.8766	High Similarity	NPC213900
0.8766	High Similarity	NPC275278
0.8765	High Similarity	NPC109061
0.8765	High Similarity	NPC103201
0.8765	High Similarity	NPC473106
0.8765	High Similarity	NPC478267
0.875	High Similarity	NPC67629
0.875	High Similarity	NPC79736
0.875	High Similarity	NPC318432
0.8743	High Similarity	NPC98583
0.8742	High Similarity	NPC62051
0.8734	High Similarity	NPC124842
0.8734	High Similarity	NPC75695
0.8727	High Similarity	NPC311912
0.872	High Similarity	NPC471788
0.872	High Similarity	NPC472277
0.872	High Similarity	NPC142614
0.8712	High Similarity	NPC476247
0.8712	High Similarity	NPC42797
0.8712	High Similarity	NPC472635
0.8712	High Similarity	NPC473445
0.8712	High Similarity	NPC144843
0.8704	High Similarity	NPC476373
0.8704	High Similarity	NPC21046
0.8704	High Similarity	NPC328102
0.8704	High Similarity	NPC472624
0.8701	High Similarity	NPC473090
0.8698	High Similarity	NPC267549
0.8696	High Similarity	NPC296044
0.8696	High Similarity	NPC125495
0.8696	High Similarity	NPC133984
0.8696	High Similarity	NPC167098
0.8696	High Similarity	NPC291508
0.869	High Similarity	NPC193377
0.8688	High Similarity	NPC268008
0.8683	High Similarity	NPC100251
0.8683	High Similarity	NPC65333
0.8679	High Similarity	NPC295646
0.8679	High Similarity	NPC199773
0.8675	High Similarity	NPC88557
0.8667	High Similarity	NPC207575
0.8667	High Similarity	NPC255787
0.8667	High Similarity	NPC13481
0.8667	High Similarity	NPC235610
0.8659	High Similarity	NPC18100
0.8659	High Similarity	NPC124038
0.8659	High Similarity	NPC291977
0.8659	High Similarity	NPC472281
0.8659	High Similarity	NPC205265
0.8659	High Similarity	NPC89131
0.865	High Similarity	NPC142252
0.865	High Similarity	NPC124747
0.865	High Similarity	NPC349525
0.865	High Similarity	NPC155754
0.8645	High Similarity	NPC113397
0.8642	High Similarity	NPC94220
0.8642	High Similarity	NPC166456
0.8642	High Similarity	NPC7543
0.8642	High Similarity	NPC98083
0.8642	High Similarity	NPC24339
0.8642	High Similarity	NPC478269
0.8634	High Similarity	NPC195796
0.8634	High Similarity	NPC228357
0.8634	High Similarity	NPC291878
0.8634	High Similarity	NPC35038
0.8634	High Similarity	NPC471405
0.8634	High Similarity	NPC278778
0.8627	High Similarity	NPC326065
0.8625	High Similarity	NPC194095
0.8625	High Similarity	NPC191046
0.8625	High Similarity	NPC327032
0.8623	High Similarity	NPC476365
0.8623	High Similarity	NPC52598
0.8614	High Similarity	NPC186392
0.8614	High Similarity	NPC473818
0.8608	High Similarity	NPC473091
0.8608	High Similarity	NPC261322
0.8606	High Similarity	NPC108433
0.8606	High Similarity	NPC300053
0.8606	High Similarity	NPC41689
0.8599	High Similarity	NPC473408
0.8598	High Similarity	NPC81679
0.8598	High Similarity	NPC249070
0.8596	High Similarity	NPC475996
0.8596	High Similarity	NPC53680
0.8596	High Similarity	NPC208797
0.8589	High Similarity	NPC476283
0.8589	High Similarity	NPC36217
0.8589	High Similarity	NPC47623
0.8589	High Similarity	NPC24627
0.8581	High Similarity	NPC50954
0.8581	High Similarity	NPC160378
0.858	High Similarity	NPC226759
0.858	High Similarity	NPC474055
0.858	High Similarity	NPC472598
0.858	High Similarity	NPC470827
0.858	High Similarity	NPC108456
0.858	High Similarity	NPC299520
0.858	High Similarity	NPC129684
0.858	High Similarity	NPC27337
0.8571	High Similarity	NPC10205
0.8571	High Similarity	NPC470327
0.8571	High Similarity	NPC477503
0.8571	High Similarity	NPC80489
0.8571	High Similarity	NPC203757
0.8571	High Similarity	NPC271848
0.8571	High Similarity	NPC81332
0.8571	High Similarity	NPC262580
0.8571	High Similarity	NPC289396
0.8571	High Similarity	NPC200761
0.8571	High Similarity	NPC45849
0.8571	High Similarity	NPC212038
0.8563	High Similarity	NPC288813
0.8563	High Similarity	NPC202428
0.8563	High Similarity	NPC266545
0.8563	High Similarity	NPC476279
0.8562	High Similarity	NPC157898
0.8562	High Similarity	NPC3744
0.8562	High Similarity	NPC137125
0.8554	High Similarity	NPC263212
0.8554	High Similarity	NPC291742
0.8554	High Similarity	NPC119589
0.8553	High Similarity	NPC300329
0.8545	High Similarity	NPC100425
0.8545	High Similarity	NPC308156
0.8545	High Similarity	NPC100420
0.8544	High Similarity	NPC107636
0.8537	High Similarity	NPC266314
0.8537	High Similarity	NPC26326
0.8537	High Similarity	NPC471499
0.8537	High Similarity	NPC131905
0.8537	High Similarity	NPC472634
0.8537	High Similarity	NPC112418
0.8537	High Similarity	NPC158188
0.8535	High Similarity	NPC39361

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 NPC469889 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	879
0.2-0.3	1631
0.3-0.4	2492
0.4-0.5	1974
0.5-0.6	1068
0.6-0.7	592
0.7-0.8	175
0.8-0.85	28
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8868	High Similarity	NPD4868	Clinical (unspecified phase)
0.8563	High Similarity	NPD5844	Phase 1
0.8509	High Similarity	NPD2393	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD1934	Approved
0.8393	Intermediate Similarity	NPD3818	Discontinued
0.8387	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6166	Phase 2
0.8373	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8293	Intermediate Similarity	NPD3882	Suspended
0.8291	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5494	Approved
0.8246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7075	Discontinued
0.8232	Intermediate Similarity	NPD3817	Phase 2
0.8218	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD4628	Phase 3
0.8204	Intermediate Similarity	NPD7199	Phase 2
0.8198	Intermediate Similarity	NPD6559	Discontinued
0.8193	Intermediate Similarity	NPD6234	Discontinued
0.8171	Intermediate Similarity	NPD2801	Approved
0.8171	Intermediate Similarity	NPD1465	Phase 2
0.8137	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7074	Phase 3
0.8079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7819	Suspended
0.8049	Intermediate Similarity	NPD7411	Suspended
0.8023	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7989	Intermediate Similarity	NPD7685	Pre-registration
0.7988	Intermediate Similarity	NPD4380	Phase 2
0.7977	Intermediate Similarity	NPD7472	Approved
0.7976	Intermediate Similarity	NPD919	Approved
0.7964	Intermediate Similarity	NPD4966	Approved
0.7964	Intermediate Similarity	NPD4965	Approved
0.7964	Intermediate Similarity	NPD4967	Phase 2
0.795	Intermediate Similarity	NPD1511	Approved
0.7943	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6190	Approved
0.7911	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD8127	Discontinued
0.7865	Intermediate Similarity	NPD8434	Phase 2
0.7861	Intermediate Similarity	NPD7228	Approved
0.7857	Intermediate Similarity	NPD7768	Phase 2
0.7853	Intermediate Similarity	NPD1512	Approved
0.7849	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7829	Intermediate Similarity	NPD6797	Phase 2
0.7818	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD3226	Approved
0.7811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD8312	Approved
0.7797	Intermediate Similarity	NPD8313	Approved
0.7791	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD9494	Approved
0.7778	Intermediate Similarity	NPD6959	Discontinued
0.7742	Intermediate Similarity	NPD6798	Discontinued
0.774	Intermediate Similarity	NPD7808	Phase 3
0.7738	Intermediate Similarity	NPD8455	Phase 2
0.773	Intermediate Similarity	NPD6799	Approved
0.7711	Intermediate Similarity	NPD7458	Discontinued
0.7707	Intermediate Similarity	NPD6355	Discontinued
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7683	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD2534	Approved
0.7683	Intermediate Similarity	NPD2532	Approved
0.7683	Intermediate Similarity	NPD2533	Approved
0.7674	Intermediate Similarity	NPD1247	Approved
0.7673	Intermediate Similarity	NPD2799	Discontinued
0.7665	Intermediate Similarity	NPD6599	Discontinued
0.7654	Intermediate Similarity	NPD3750	Approved
0.7643	Intermediate Similarity	NPD4060	Phase 1
0.764	Intermediate Similarity	NPD1549	Phase 2
0.7636	Intermediate Similarity	NPD6273	Approved
0.763	Intermediate Similarity	NPD7229	Phase 3
0.7628	Intermediate Similarity	NPD3764	Approved
0.7614	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3749	Approved
0.7595	Intermediate Similarity	NPD447	Suspended
0.759	Intermediate Similarity	NPD920	Approved
0.7588	Intermediate Similarity	NPD5402	Approved
0.7586	Intermediate Similarity	NPD3926	Phase 2
0.758	Intermediate Similarity	NPD6233	Phase 2
0.7578	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1608	Approved
0.7546	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4110	Phase 3
0.7546	Intermediate Similarity	NPD7003	Approved
0.7545	Intermediate Similarity	NPD1653	Approved
0.7532	Intermediate Similarity	NPD1613	Approved
0.7532	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7038	Approved
0.7486	Intermediate Similarity	NPD7039	Approved
0.7485	Intermediate Similarity	NPD5403	Approved
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6002	Phase 3
0.7469	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7266	Discontinued
0.7469	Intermediate Similarity	NPD2344	Approved
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7469	Intermediate Similarity	NPD6004	Phase 3
0.7469	Intermediate Similarity	NPD6005	Phase 3
0.7458	Intermediate Similarity	NPD7177	Discontinued
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7033	Discontinued
0.7453	Intermediate Similarity	NPD1510	Phase 2
0.7452	Intermediate Similarity	NPD3027	Phase 3
0.7439	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD8166	Discontinued
0.7419	Intermediate Similarity	NPD2797	Approved
0.7412	Intermediate Similarity	NPD6386	Approved
0.7412	Intermediate Similarity	NPD6385	Approved
0.7405	Intermediate Similarity	NPD3268	Approved
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7405	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7240	Approved
0.7377	Intermediate Similarity	NPD8150	Discontinued
0.7375	Intermediate Similarity	NPD1933	Approved
0.7368	Intermediate Similarity	NPD17	Approved
0.7365	Intermediate Similarity	NPD5401	Approved
0.7346	Intermediate Similarity	NPD3748	Approved
0.7326	Intermediate Similarity	NPD5760	Phase 2
0.7326	Intermediate Similarity	NPD5761	Phase 2
0.7325	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2861	Phase 2
0.7312	Intermediate Similarity	NPD1240	Approved
0.7301	Intermediate Similarity	NPD2438	Suspended
0.7289	Intermediate Similarity	NPD2309	Approved
0.7288	Intermediate Similarity	NPD5242	Approved
0.7278	Intermediate Similarity	NPD6832	Phase 2
0.7278	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD6674	Discontinued
0.7273	Intermediate Similarity	NPD1243	Approved
0.7273	Intermediate Similarity	NPD2800	Approved
0.7249	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4308	Phase 3
0.7238	Intermediate Similarity	NPD5953	Discontinued
0.7237	Intermediate Similarity	NPD9545	Approved
0.7233	Intermediate Similarity	NPD7095	Approved
0.7222	Intermediate Similarity	NPD1607	Approved
0.7209	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD943	Approved
0.7198	Intermediate Similarity	NPD6765	Approved
0.7198	Intermediate Similarity	NPD6764	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7195	Intermediate Similarity	NPD5408	Approved
0.7195	Intermediate Similarity	NPD5404	Approved
0.7195	Intermediate Similarity	NPD5406	Approved
0.7195	Intermediate Similarity	NPD5405	Approved
0.7193	Intermediate Similarity	NPD3455	Phase 2
0.7184	Intermediate Similarity	NPD5353	Approved
0.7178	Intermediate Similarity	NPD7097	Phase 1
0.7174	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3751	Discontinued
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7549	Discontinued
0.7158	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD7440	Discontinued
0.7135	Intermediate Similarity	NPD5711	Approved
0.7135	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5710	Approved
0.7134	Intermediate Similarity	NPD1283	Approved
0.7127	Intermediate Similarity	NPD7286	Phase 2
0.7121	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7783	Phase 2
0.7118	Intermediate Similarity	NPD5049	Phase 3
0.7117	Intermediate Similarity	NPD6653	Approved
0.7113	Intermediate Similarity	NPD7680	Approved
0.7113	Intermediate Similarity	NPD7435	Discontinued
0.711	Intermediate Similarity	NPD6873	Phase 2
0.7107	Intermediate Similarity	NPD8151	Discontinued
0.7099	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2979	Phase 3
0.7099	Intermediate Similarity	NPD3620	Phase 2
0.7091	Intermediate Similarity	NPD6100	Approved
0.7091	Intermediate Similarity	NPD4476	Approved
0.7091	Intermediate Similarity	NPD4477	Approved
0.7091	Intermediate Similarity	NPD6099	Approved
0.7089	Intermediate Similarity	NPD3266	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