NPASS Compound

Structure

NPC471244 OpenBabel07101718322D 29 33 0 0 1 0 0 0 0 0999 V2000 -2.5092 -3.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6123 -2.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5681 -1.0432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0852 -0.2068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6728 -2.6271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4264 -0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7483 -1.1291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6023 -1.7387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2327 -1.1768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7281 -0.3477 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2046 -0.6955 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6023 -1.7387 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.6955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2912 -0.9619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0927 0.3796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.6955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6023 -1.0432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6023 -1.0432 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2046 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6023 0.3477 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4387 -2.2216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5638 -1.5974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3076 1.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 0.4829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0852 1.1841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6728 -1.6613 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 5 1 0 0 0 0 2 10 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 28 1 0 0 0 0 6 7 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 6 1 1 0 0 0 11 16 1 0 0 0 0 12 20 1 1 0 0 0 12 21 1 0 0 0 0 13 20 1 1 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 1 0 0 0 15 21 1 0 0 0 0 15 24 2 0 0 0 0 16 21 1 6 0 0 0 16 25 1 0 0 0 0 17 22 1 6 0 0 0 17 26 1 0 0 0 0 18 20 1 6 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 21 22 1 0 0 0 0 22 27 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.21
Volume:	402.545
LogP:	1.741
LogD:	1.156
LogS:	-3.993
# Rotatable Bonds:	2
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	7.02
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.038
MDCK Permeability:	7.037073373794556e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307
Plasma Protein Binding (PPB):	60.798336029052734%
Volume Distribution (VD):	1.16
Pgp-substrate:	55.04238510131836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	2.401
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.835
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.481
Carcinogencity:	0.235
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC471244

Natural Product ID:	NPC471244
*Common Name:**	CEINIYPVMZSXKB-UCMBFLOESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CEINIYPVMZSXKB-UCMBFLOESA-N
Standard InCHI:	InChI=1S/C22H32O7/c1-5-28-18-20-12-7-6-11-10(2)15(24)21(12,16(11)25)22(27,29-18)17(26)14(20)19(3,4)9-8-13(20)23/h11-14,16-18,23,25-27H,2,5-9H2,1,3-4H3/t11-,12-,13-,14+,16+,17-,18+,20-,21-,22-/m0/s1
SMILES:	CCOC1C23C4CCC5C(C4(C(=O)C5=C)C(O1)(C(C2C(CCC3O)(C)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2407383
PubChem CID:	73353584
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[23819871]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17800	Isodon rosthornii	Species	Lamiaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3900.0	nM	PMID[522225]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	7800.0	nM	PMID[522225]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8400.0	nM	PMID[522225]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[522225]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[522225]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5900.0	nM	PMID[522225]

☑ 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 NPC471244 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	298
0.1-0.2	2104
0.2-0.3	6225
0.3-0.4	10493
0.4-0.5	10591
0.5-0.6	6280
0.6-0.7	3792
0.7-0.8	2155
0.8-0.85	625
0.85-0.9	60
0.9-0.95	38
0.95-1	36

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC63244
0.9808	High Similarity	NPC471245
0.9806	High Similarity	NPC471476
0.9717	High Similarity	NPC88945
0.9714	High Similarity	NPC94141
0.9712	High Similarity	NPC122339
0.9623	High Similarity	NPC17165
0.9619	High Similarity	NPC473303
0.9619	High Similarity	NPC145625
0.9619	High Similarity	NPC157929
0.9615	High Similarity	NPC473324
0.9612	High Similarity	NPC89860
0.9612	High Similarity	NPC189663
0.9533	High Similarity	NPC229752
0.9528	High Similarity	NPC132668
0.9528	High Similarity	NPC471248
0.9519	High Similarity	NPC118721
0.9519	High Similarity	NPC469744
0.9519	High Similarity	NPC252679
0.9444	High Similarity	NPC78836
0.9444	High Similarity	NPC473304
0.9434	High Similarity	NPC474927
0.9423	High Similarity	NPC55973
0.9417	High Similarity	NPC307660
0.9417	High Similarity	NPC130511
0.934	High Similarity	NPC213320
0.9333	High Similarity	NPC102741
0.9327	High Similarity	NPC469746
0.9327	High Similarity	NPC67745
0.9327	High Similarity	NPC471461
0.9252	High Similarity	NPC473397
0.9252	High Similarity	NPC473352
0.9245	High Similarity	NPC471093
0.9245	High Similarity	NPC137104
0.9245	High Similarity	NPC320383
0.9245	High Similarity	NPC474786
0.9238	High Similarity	NPC473410
0.9238	High Similarity	NPC469984
0.9238	High Similarity	NPC471094
0.9238	High Similarity	NPC469733
0.9238	High Similarity	NPC469729
0.9231	High Similarity	NPC12823
0.9167	High Similarity	NPC471252
0.9159	High Similarity	NPC329953
0.9159	High Similarity	NPC29505
0.9151	High Similarity	NPC131903
0.9151	High Similarity	NPC274827
0.9143	High Similarity	NPC471474
0.9065	High Similarity	NPC85391
0.9057	High Similarity	NPC63841
0.9048	High Similarity	NPC4115
0.9048	High Similarity	NPC56656
0.9029	High Similarity	NPC14634
0.8981	High Similarity	NPC471243
0.8962	High Similarity	NPC186054
0.8952	High Similarity	NPC202793
0.8942	High Similarity	NPC475803
0.8942	High Similarity	NPC309388
0.8909	High Similarity	NPC243354
0.8899	High Similarity	NPC472719
0.8899	High Similarity	NPC207845
0.8879	High Similarity	NPC232133
0.8818	High Similarity	NPC194273
0.8807	High Similarity	NPC56025
0.8807	High Similarity	NPC274833
0.8796	High Similarity	NPC8431
0.8796	High Similarity	NPC469983
0.8704	High Similarity	NPC231278
0.8704	High Similarity	NPC218123
0.8704	High Similarity	NPC273155
0.8704	High Similarity	NPC112895
0.8679	High Similarity	NPC277074
0.8679	High Similarity	NPC209298
0.8679	High Similarity	NPC139347
0.8661	High Similarity	NPC472718
0.8649	High Similarity	NPC73986
0.8611	High Similarity	NPC166993
0.8611	High Similarity	NPC96333
0.8611	High Similarity	NPC88833
0.8598	High Similarity	NPC474558
0.8598	High Similarity	NPC13149
0.8598	High Similarity	NPC470167
0.8584	High Similarity	NPC218970
0.8545	High Similarity	NPC98069
0.8545	High Similarity	NPC49730
0.8519	High Similarity	NPC200957
0.8519	High Similarity	NPC103172
0.8519	High Similarity	NPC138908
0.8519	High Similarity	NPC164600
0.8505	High Similarity	NPC122811
0.8505	High Similarity	NPC87927
0.8505	High Similarity	NPC107385
0.8491	Intermediate Similarity	NPC52899
0.8491	Intermediate Similarity	NPC289148
0.8491	Intermediate Similarity	NPC471790
0.8491	Intermediate Similarity	NPC163963
0.8482	Intermediate Similarity	NPC320118
0.8476	Intermediate Similarity	NPC474793
0.8475	Intermediate Similarity	NPC47113
0.8475	Intermediate Similarity	NPC174367
0.8468	Intermediate Similarity	NPC11035
0.844	Intermediate Similarity	NPC61071
0.8426	Intermediate Similarity	NPC101842
0.8426	Intermediate Similarity	NPC301787
0.8411	Intermediate Similarity	NPC76866
0.8411	Intermediate Similarity	NPC148628
0.8411	Intermediate Similarity	NPC286519
0.8411	Intermediate Similarity	NPC88203
0.8411	Intermediate Similarity	NPC214946
0.8411	Intermediate Similarity	NPC246736
0.8411	Intermediate Similarity	NPC304832
0.8396	Intermediate Similarity	NPC127408
0.8396	Intermediate Similarity	NPC287676
0.8396	Intermediate Similarity	NPC291785
0.8396	Intermediate Similarity	NPC470388
0.8393	Intermediate Similarity	NPC205534
0.8393	Intermediate Similarity	NPC470543
0.8393	Intermediate Similarity	NPC243572
0.8376	Intermediate Similarity	NPC28532
0.8349	Intermediate Similarity	NPC222833
0.8348	Intermediate Similarity	NPC475632
0.8348	Intermediate Similarity	NPC86020
0.8319	Intermediate Similarity	NPC146563
0.8319	Intermediate Similarity	NPC260665
0.8319	Intermediate Similarity	NPC102619
0.8319	Intermediate Similarity	NPC273962
0.8318	Intermediate Similarity	NPC252614
0.8318	Intermediate Similarity	NPC46848
0.8318	Intermediate Similarity	NPC236585
0.8304	Intermediate Similarity	NPC272242
0.8304	Intermediate Similarity	NPC471251
0.8302	Intermediate Similarity	NPC471038
0.8302	Intermediate Similarity	NPC16911
0.8302	Intermediate Similarity	NPC78427
0.8291	Intermediate Similarity	NPC470478
0.8288	Intermediate Similarity	NPC246205
0.8288	Intermediate Similarity	NPC473844
0.8288	Intermediate Similarity	NPC471250
0.8288	Intermediate Similarity	NPC91583
0.8288	Intermediate Similarity	NPC51947
0.8288	Intermediate Similarity	NPC240125
0.8276	Intermediate Similarity	NPC161738
0.8261	Intermediate Similarity	NPC309433
0.8261	Intermediate Similarity	NPC470171
0.8261	Intermediate Similarity	NPC477252
0.8261	Intermediate Similarity	NPC156651
0.8257	Intermediate Similarity	NPC98603
0.825	Intermediate Similarity	NPC305496
0.8246	Intermediate Similarity	NPC74727
0.8246	Intermediate Similarity	NPC54395
0.8246	Intermediate Similarity	NPC102088
0.8246	Intermediate Similarity	NPC477580
0.8241	Intermediate Similarity	NPC470172
0.8241	Intermediate Similarity	NPC275990
0.8235	Intermediate Similarity	NPC469841
0.8235	Intermediate Similarity	NPC248202
0.8235	Intermediate Similarity	NPC469842
0.823	Intermediate Similarity	NPC210420
0.823	Intermediate Similarity	NPC474265
0.822	Intermediate Similarity	NPC475431
0.8214	Intermediate Similarity	NPC98633
0.8214	Intermediate Similarity	NPC475317
0.8214	Intermediate Similarity	NPC154856
0.8214	Intermediate Similarity	NPC52241
0.8214	Intermediate Similarity	NPC130302
0.8208	Intermediate Similarity	NPC76486
0.8205	Intermediate Similarity	NPC471406
0.8205	Intermediate Similarity	NPC108072
0.8205	Intermediate Similarity	NPC475187
0.8205	Intermediate Similarity	NPC281840
0.8198	Intermediate Similarity	NPC88744
0.8198	Intermediate Similarity	NPC230888
0.819	Intermediate Similarity	NPC239293
0.819	Intermediate Similarity	NPC231060
0.819	Intermediate Similarity	NPC41070
0.819	Intermediate Similarity	NPC84018
0.819	Intermediate Similarity	NPC138245
0.8182	Intermediate Similarity	NPC311534
0.8182	Intermediate Similarity	NPC210178
0.8182	Intermediate Similarity	NPC285927
0.8174	Intermediate Similarity	NPC137414
0.8174	Intermediate Similarity	NPC469820
0.8174	Intermediate Similarity	NPC469823
0.8173	Intermediate Similarity	NPC144739
0.8173	Intermediate Similarity	NPC181594
0.8165	Intermediate Similarity	NPC216114
0.8165	Intermediate Similarity	NPC473406
0.8165	Intermediate Similarity	NPC96217
0.8158	Intermediate Similarity	NPC293038
0.8158	Intermediate Similarity	NPC62696
0.8148	Intermediate Similarity	NPC148279
0.8148	Intermediate Similarity	NPC470168
0.8142	Intermediate Similarity	NPC91838
0.8142	Intermediate Similarity	NPC94650
0.8142	Intermediate Similarity	NPC285410
0.8142	Intermediate Similarity	NPC275668
0.8142	Intermediate Similarity	NPC263827
0.8142	Intermediate Similarity	NPC204392
0.8142	Intermediate Similarity	NPC1876
0.8142	Intermediate Similarity	NPC240734

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 NPC471244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	2455
0.2-0.3	4022
0.3-0.4	1496
0.4-0.5	450
0.5-0.6	252
0.6-0.7	135
0.7-0.8	36
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8108	Intermediate Similarity	NPD6412	Phase 2
0.8067	Intermediate Similarity	NPD6370	Approved
0.8	Intermediate Similarity	NPD8328	Phase 3
0.7949	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD6054	Approved
0.7886	Intermediate Similarity	NPD7736	Approved
0.7845	Intermediate Similarity	NPD8133	Approved
0.7823	Intermediate Similarity	NPD7319	Approved
0.7807	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6059	Approved
0.7724	Intermediate Similarity	NPD7507	Approved
0.7686	Intermediate Similarity	NPD6015	Approved
0.7686	Intermediate Similarity	NPD6016	Approved
0.7661	Intermediate Similarity	NPD8293	Discontinued
0.7642	Intermediate Similarity	NPD7492	Approved
0.7623	Intermediate Similarity	NPD5988	Approved
0.7581	Intermediate Similarity	NPD6616	Approved
0.7565	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD7078	Approved
0.7459	Intermediate Similarity	NPD6319	Approved
0.7414	Intermediate Similarity	NPD6686	Approved
0.7355	Intermediate Similarity	NPD6009	Approved
0.7311	Intermediate Similarity	NPD6882	Approved
0.7288	Intermediate Similarity	NPD4634	Approved
0.7258	Intermediate Similarity	NPD8033	Approved
0.725	Intermediate Similarity	NPD4632	Approved
0.7236	Intermediate Similarity	NPD7516	Approved
0.7213	Intermediate Similarity	NPD7115	Discovery
0.7188	Intermediate Similarity	NPD6033	Approved
0.7177	Intermediate Similarity	NPD8294	Approved
0.7177	Intermediate Similarity	NPD8377	Approved
0.7167	Intermediate Similarity	NPD8297	Approved
0.7154	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD7327	Approved
0.712	Intermediate Similarity	NPD8296	Approved
0.712	Intermediate Similarity	NPD8517	Approved
0.712	Intermediate Similarity	NPD8380	Approved
0.712	Intermediate Similarity	NPD8379	Approved
0.712	Intermediate Similarity	NPD8513	Phase 3
0.712	Intermediate Similarity	NPD8516	Approved
0.712	Intermediate Similarity	NPD8515	Approved
0.712	Intermediate Similarity	NPD8378	Approved
0.712	Intermediate Similarity	NPD8335	Approved
0.7119	Intermediate Similarity	NPD6899	Approved
0.7119	Intermediate Similarity	NPD6881	Approved
0.7094	Intermediate Similarity	NPD7128	Approved
0.7094	Intermediate Similarity	NPD6402	Approved
0.7094	Intermediate Similarity	NPD5739	Approved
0.7094	Intermediate Similarity	NPD6675	Approved
0.7091	Intermediate Similarity	NPD8034	Phase 2
0.7091	Intermediate Similarity	NPD8035	Phase 2
0.7083	Intermediate Similarity	NPD6650	Approved
0.7083	Intermediate Similarity	NPD6649	Approved
0.7059	Intermediate Similarity	NPD6372	Approved
0.7059	Intermediate Similarity	NPD6373	Approved
0.7034	Intermediate Similarity	NPD5697	Approved
0.7008	Intermediate Similarity	NPD6067	Discontinued
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.6984	Remote Similarity	NPD7503	Approved
0.6975	Remote Similarity	NPD7320	Approved
0.6957	Remote Similarity	NPD4696	Approved
0.6957	Remote Similarity	NPD5286	Approved
0.6957	Remote Similarity	NPD5285	Approved
0.6949	Remote Similarity	NPD6008	Approved
0.6942	Remote Similarity	NPD8130	Phase 1
0.6942	Remote Similarity	NPD6869	Approved
0.6942	Remote Similarity	NPD6617	Approved
0.6942	Remote Similarity	NPD6847	Approved
0.6937	Remote Similarity	NPD6079	Approved
0.693	Remote Similarity	NPD4755	Approved
0.6917	Remote Similarity	NPD6014	Approved
0.6917	Remote Similarity	NPD6013	Approved
0.6917	Remote Similarity	NPD6012	Approved
0.6909	Remote Similarity	NPD5328	Approved
0.6891	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD7604	Phase 2
0.6875	Remote Similarity	NPD8171	Discontinued
0.6875	Remote Similarity	NPD6399	Phase 3
0.6852	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5983	Phase 2
0.685	Remote Similarity	NPD6921	Approved
0.6838	Remote Similarity	NPD5224	Approved
0.6838	Remote Similarity	NPD5226	Approved
0.6838	Remote Similarity	NPD4633	Approved
0.6838	Remote Similarity	NPD5225	Approved
0.6838	Remote Similarity	NPD5211	Phase 2
0.6833	Remote Similarity	NPD6011	Approved
0.681	Remote Similarity	NPD4700	Approved
0.678	Remote Similarity	NPD5175	Approved
0.678	Remote Similarity	NPD5174	Approved
0.6769	Remote Similarity	NPD6336	Discontinued
0.6752	Remote Similarity	NPD5223	Approved
0.6724	Remote Similarity	NPD4225	Approved
0.6723	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD5221	Approved
0.6696	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4788	Approved
0.6639	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7902	Approved
0.6638	Remote Similarity	NPD5173	Approved
0.6636	Remote Similarity	NPD3618	Phase 1
0.6606	Remote Similarity	NPD4786	Approved
0.6587	Remote Similarity	NPD6274	Approved
0.6581	Remote Similarity	NPD7638	Approved
0.6579	Remote Similarity	NPD4202	Approved
0.6567	Remote Similarity	NPD5956	Approved
0.6562	Remote Similarity	NPD7101	Approved
0.6562	Remote Similarity	NPD7100	Approved
0.6557	Remote Similarity	NPD4729	Approved
0.6557	Remote Similarity	NPD4730	Approved
0.6557	Remote Similarity	NPD5128	Approved
0.6529	Remote Similarity	NPD4768	Approved
0.6529	Remote Similarity	NPD4767	Approved
0.6525	Remote Similarity	NPD7640	Approved
0.6525	Remote Similarity	NPD7639	Approved
0.6522	Remote Similarity	NPD7748	Approved
0.65	Remote Similarity	NPD4754	Approved
0.6496	Remote Similarity	NPD6084	Phase 2
0.6496	Remote Similarity	NPD6083	Phase 2
0.6491	Remote Similarity	NPD6411	Approved
0.6491	Remote Similarity	NPD7515	Phase 2
0.6486	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6335	Approved
0.6466	Remote Similarity	NPD8074	Phase 3
0.6457	Remote Similarity	NPD6940	Discontinued
0.6452	Remote Similarity	NPD5251	Approved
0.6452	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5248	Approved
0.6452	Remote Similarity	NPD5249	Phase 3
0.6452	Remote Similarity	NPD5250	Approved
0.6452	Remote Similarity	NPD5247	Approved
0.6452	Remote Similarity	NPD6371	Approved
0.6422	Remote Similarity	NPD3667	Approved
0.6406	Remote Similarity	NPD6317	Approved
0.64	Remote Similarity	NPD5216	Approved
0.64	Remote Similarity	NPD5215	Approved
0.64	Remote Similarity	NPD5217	Approved
0.6389	Remote Similarity	NPD6928	Phase 2
0.6381	Remote Similarity	NPD3703	Phase 2
0.6379	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7900	Approved
0.6357	Remote Similarity	NPD6314	Approved
0.6357	Remote Similarity	NPD6313	Approved
0.6355	Remote Similarity	NPD6114	Approved
0.6355	Remote Similarity	NPD6697	Approved
0.6355	Remote Similarity	NPD6115	Approved
0.6355	Remote Similarity	NPD6118	Approved
0.6336	Remote Similarity	NPD6909	Approved
0.6336	Remote Similarity	NPD6908	Approved
0.6336	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1700	Approved
0.633	Remote Similarity	NPD1779	Approved
0.633	Remote Similarity	NPD1780	Approved
0.6328	Remote Similarity	NPD6868	Approved
0.6325	Remote Similarity	NPD5210	Approved
0.6325	Remote Similarity	NPD4629	Approved
0.632	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5169	Approved
0.632	Remote Similarity	NPD5135	Approved
0.6316	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD4753	Phase 2
0.6316	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD3666	Approved
0.6306	Remote Similarity	NPD3665	Phase 1
0.6306	Remote Similarity	NPD3133	Approved
0.6303	Remote Similarity	NPD5696	Approved
0.6296	Remote Similarity	NPD8336	Approved
0.6296	Remote Similarity	NPD8337	Approved
0.6283	Remote Similarity	NPD3573	Approved
0.627	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5127	Approved
0.6262	Remote Similarity	NPD6116	Phase 1
0.6239	Remote Similarity	NPD5282	Discontinued
0.6232	Remote Similarity	NPD8338	Approved
0.6228	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6053	Discontinued
0.6216	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3669	Approved
0.6212	Remote Similarity	NPD8269	Approved
0.6212	Remote Similarity	NPD8268	Approved
0.6212	Remote Similarity	NPD8267	Approved
0.6212	Remote Similarity	NPD8266	Approved
0.621	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7334	Approved
0.6195	Remote Similarity	NPD6409	Approved
0.6195	Remote Similarity	NPD5330	Approved
0.6195	Remote Similarity	NPD6684	Approved
0.6195	Remote Similarity	NPD7146	Approved
0.6195	Remote Similarity	NPD7521	Approved
0.6186	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5695	Phase 3
0.6183	Remote Similarity	NPD4522	Approved
0.6168	Remote Similarity	NPD6117	Approved
0.6165	Remote Similarity	NPD8080	Discontinued

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