NPASS Compound

Structure

NPC13149 OpenBabel07101719512D 25 29 0 0 1 0 0 0 0 0999 V2000 0.8336 0.7282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0574 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 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 1.0817 2.2140 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1415 1.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4614 2.7398 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8433 1.1641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7130 3.7077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3057 0.4754 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 10 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 17 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 18 1 0 0 0 0 9 25 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 8 1 1 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 1 0 0 0 13 20 1 1 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 15 20 1 6 0 0 0 15 23 1 0 0 0 0 16 18 1 1 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 18 6 1 6 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 20 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.19
Volume:	350.372
LogP:	1.54
LogD:	1.487
LogS:	-3.608
# Rotatable Bonds:	0
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	6.735
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.137
MDCK Permeability:	1.137185790867079e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.494

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.587
Plasma Protein Binding (PPB):	64.15960693359375%
Volume Distribution (VD):	1.303
Pgp-substrate:	52.43939208984375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.709
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.128
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	2.73
Half-life (T1/2):	0.337

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.772
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.557
Carcinogencity:	0.126
Eye Corrosion:	0.009
Eye Irritation:	0.047
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC13149

Natural Product ID:	NPC13149
*Common Name:**	Pseudoirroratin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NDYPVJHBSKUXPP-VWIBHASISA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-10-11-8-19(24)16-18(9-25-19)6-4-5-17(2,3)12(18)7-13(21)20(16,14(10)22)15(11)23/h11-13,15-16,21,23-24H,1,4-9H2,2-3H3/t11-,12+,13+,15+,16+,18-,19+,20+/m0/s1
SMILES:	C=C1[C@@H]2C[C@@]3([C@H]4[C@@]5(CCCC(C)(C)[C@H]5C[C@H]([C@@]4(C1=O)[C@@H]2O)O)CO3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517614
PubChem CID:	637422
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
NPO33194	isodon pseudo-irrorata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858760]

☑ 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	7
Others	15

Activity Type	# Activity
Cell Line	20
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	750.0	nM	PMID[543925]
NPT2345	Cell Line	SW626	Homo sapiens	IC50	=	570.0	nM	PMID[543925]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	2590.0	nM	PMID[543925]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2590.0	nM	PMID[543925]
NPT307	Cell Line	HOS	Homo sapiens	IC50	=	1440.0	nM	PMID[543925]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	13.8	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	30.2	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	33.9	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	21.1	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	24.7	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	26.2	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	14.7	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	27.8	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	18.3	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	11.1	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	17.0	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	10.0	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	3.1	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	5.3	%	PMID[543926]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	8.5	%	PMID[543926]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4900.0	nM	PMID[543926]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5900.0	nM	PMID[543926]

☑ 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 NPC13149 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	254
0.1-0.2	1772
0.2-0.3	6019
0.3-0.4	10121
0.4-0.5	10707
0.5-0.6	6154
0.6-0.7	5853
0.7-0.8	1504
0.8-0.85	162
0.85-0.9	129
0.9-0.95	21
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC309388
0.9388	High Similarity	NPC475803
0.9307	High Similarity	NPC469729
0.9307	High Similarity	NPC469733
0.9293	High Similarity	NPC87927
0.9286	High Similarity	NPC471790
0.9208	High Similarity	NPC469746
0.9167	High Similarity	NPC231060
0.9167	High Similarity	NPC138245
0.9167	High Similarity	NPC84018
0.9118	High Similarity	NPC55973
0.9109	High Similarity	NPC4115
0.9109	High Similarity	NPC12823
0.91	High Similarity	NPC139347
0.9091	High Similarity	NPC289148
0.9091	High Similarity	NPC52899
0.9091	High Similarity	NPC163963
0.9091	High Similarity	NPC14634
0.9062	High Similarity	NPC302008
0.9062	High Similarity	NPC191094
0.9038	High Similarity	NPC329953
0.9038	High Similarity	NPC29505
0.9029	High Similarity	NPC252679
0.9029	High Similarity	NPC469744
0.9029	High Similarity	NPC118721
0.902	High Similarity	NPC88833
0.902	High Similarity	NPC96333
0.902	High Similarity	NPC67745
0.902	High Similarity	NPC471461
0.901	High Similarity	NPC202793
0.9	High Similarity	NPC88203
0.9	High Similarity	NPC286519
0.9	High Similarity	NPC304832
0.9	High Similarity	NPC76866
0.9	High Similarity	NPC214946
0.9	High Similarity	NPC148628
0.9	High Similarity	NPC246736
0.899	High Similarity	NPC287676
0.8958	High Similarity	NPC59170
0.8958	High Similarity	NPC144739
0.8958	High Similarity	NPC181594
0.8952	High Similarity	NPC473303
0.8942	High Similarity	NPC473324
0.8942	High Similarity	NPC471093
0.8932	High Similarity	NPC112895
0.8932	High Similarity	NPC218123
0.8932	High Similarity	NPC89860
0.8932	High Similarity	NPC189663
0.8932	High Similarity	NPC231278
0.8911	High Similarity	NPC216114
0.89	High Similarity	NPC46848
0.8889	High Similarity	NPC471038
0.8889	High Similarity	NPC16911
0.8889	High Similarity	NPC78427
0.8878	High Similarity	NPC13949
0.8868	High Similarity	NPC471252
0.8868	High Similarity	NPC471248
0.8866	High Similarity	NPC91772
0.8866	High Similarity	NPC129004
0.8866	High Similarity	NPC289539
0.8866	High Similarity	NPC104371
0.8866	High Similarity	NPC215271
0.8866	High Similarity	NPC292374
0.8866	High Similarity	NPC29247
0.8866	High Similarity	NPC261333
0.8866	High Similarity	NPC111524
0.8866	High Similarity	NPC153775
0.8866	High Similarity	NPC101233
0.8857	High Similarity	NPC122339
0.8854	High Similarity	NPC299185
0.8854	High Similarity	NPC476168
0.8835	High Similarity	NPC61071
0.8824	High Similarity	NPC101842
0.8824	High Similarity	NPC84928
0.8824	High Similarity	NPC98603
0.8812	High Similarity	NPC275990
0.88	High Similarity	NPC291785
0.88	High Similarity	NPC127408
0.88	High Similarity	NPC267921
0.8776	High Similarity	NPC470232
0.8776	High Similarity	NPC29112
0.8774	High Similarity	NPC471245
0.8774	High Similarity	NPC473397
0.8762	High Similarity	NPC49730
0.8762	High Similarity	NPC471476
0.8762	High Similarity	NPC98069
0.875	High Similarity	NPC261994
0.875	High Similarity	NPC180849
0.875	High Similarity	NPC470378
0.875	High Similarity	NPC149761
0.875	High Similarity	NPC80401
0.875	High Similarity	NPC63841
0.8738	High Similarity	NPC130511
0.8738	High Similarity	NPC103172
0.8738	High Similarity	NPC307660
0.8738	High Similarity	NPC164600
0.87	High Similarity	NPC28864
0.87	High Similarity	NPC20479
0.87	High Similarity	NPC38296
0.87	High Similarity	NPC98837
0.87	High Similarity	NPC474793
0.87	High Similarity	NPC89099
0.87	High Similarity	NPC162459
0.87	High Similarity	NPC38471
0.8687	High Similarity	NPC140242
0.8687	High Similarity	NPC264979
0.8687	High Similarity	NPC135548
0.8687	High Similarity	NPC329910
0.8687	High Similarity	NPC29410
0.8687	High Similarity	NPC200054
0.8679	High Similarity	NPC213320
0.8679	High Similarity	NPC63244
0.8673	High Similarity	NPC475118
0.8673	High Similarity	NPC470385
0.8673	High Similarity	NPC470386
0.8667	High Similarity	NPC102741
0.866	High Similarity	NPC278106
0.8654	High Similarity	NPC186054
0.8641	High Similarity	NPC474558
0.8624	High Similarity	NPC473304
0.8614	High Similarity	NPC470388
0.8614	High Similarity	NPC293866
0.8611	High Similarity	NPC17165
0.86	High Similarity	NPC10864
0.8598	High Similarity	NPC471244
0.8598	High Similarity	NPC145625
0.8598	High Similarity	NPC473352
0.8598	High Similarity	NPC474927
0.8586	High Similarity	NPC470229
0.8586	High Similarity	NPC98639
0.8586	High Similarity	NPC210214
0.8585	High Similarity	NPC130302
0.8571	High Similarity	NPC232133
0.8571	High Similarity	NPC473410
0.8571	High Similarity	NPC273155
0.8571	High Similarity	NPC59350
0.8571	High Similarity	NPC471094
0.8571	High Similarity	NPC469984
0.8558	High Similarity	NPC138908
0.8558	High Similarity	NPC200957
0.8558	High Similarity	NPC285927
0.8558	High Similarity	NPC37600
0.8544	High Similarity	NPC96217
0.8544	High Similarity	NPC209298
0.8544	High Similarity	NPC277074
0.8544	High Similarity	NPC159442
0.8544	High Similarity	NPC122811
0.8529	High Similarity	NPC236585
0.8529	High Similarity	NPC39683
0.8529	High Similarity	NPC148279
0.8519	High Similarity	NPC94141
0.8519	High Similarity	NPC132668
0.8505	High Similarity	NPC471243
0.85	High Similarity	NPC470387
0.8491	Intermediate Similarity	NPC469983
0.8485	Intermediate Similarity	NPC47853
0.8485	Intermediate Similarity	NPC64006
0.8476	Intermediate Similarity	NPC176949
0.8476	Intermediate Similarity	NPC166993
0.8476	Intermediate Similarity	NPC471474
0.8476	Intermediate Similarity	NPC201908
0.8469	Intermediate Similarity	NPC211403
0.8469	Intermediate Similarity	NPC250753
0.8469	Intermediate Similarity	NPC198242
0.8462	Intermediate Similarity	NPC96268
0.8455	Intermediate Similarity	NPC78836
0.8447	Intermediate Similarity	NPC272472
0.844	Intermediate Similarity	NPC243354
0.8438	Intermediate Similarity	NPC165895
0.8438	Intermediate Similarity	NPC153604
0.8438	Intermediate Similarity	NPC259009
0.8438	Intermediate Similarity	NPC174619
0.8431	Intermediate Similarity	NPC55503
0.8431	Intermediate Similarity	NPC156324
0.8431	Intermediate Similarity	NPC108371
0.8426	Intermediate Similarity	NPC157929
0.8416	Intermediate Similarity	NPC253586
0.8411	Intermediate Similarity	NPC320383
0.8411	Intermediate Similarity	NPC98633
0.8411	Intermediate Similarity	NPC85391
0.8411	Intermediate Similarity	NPC124053
0.8411	Intermediate Similarity	NPC137104
0.8411	Intermediate Similarity	NPC474786
0.8411	Intermediate Similarity	NPC255655
0.8396	Intermediate Similarity	NPC211224
0.8384	Intermediate Similarity	NPC294263
0.8381	Intermediate Similarity	NPC56656
0.8381	Intermediate Similarity	NPC295366
0.8365	Intermediate Similarity	NPC470310
0.8364	Intermediate Similarity	NPC88945
0.8364	Intermediate Similarity	NPC229752
0.835	Intermediate Similarity	NPC252614
0.835	Intermediate Similarity	NPC60947
0.835	Intermediate Similarity	NPC253886
0.835	Intermediate Similarity	NPC121218
0.8333	Intermediate Similarity	NPC471251
0.8333	Intermediate Similarity	NPC470281
0.8333	Intermediate Similarity	NPC94650
0.8333	Intermediate Similarity	NPC26270
0.8318	Intermediate Similarity	NPC274827

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 NPC13149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	2200
0.2-0.3	4083
0.3-0.4	1705
0.4-0.5	452
0.5-0.6	219
0.6-0.7	169
0.7-0.8	70
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
0.807	Intermediate Similarity	NPD6054	Approved
0.8	Intermediate Similarity	NPD6015	Approved
0.8	Intermediate Similarity	NPD6016	Approved
0.7931	Intermediate Similarity	NPD5988	Approved
0.7931	Intermediate Similarity	NPD6370	Approved
0.7913	Intermediate Similarity	NPD6059	Approved
0.7797	Intermediate Similarity	NPD7492	Approved
0.775	Intermediate Similarity	NPD7736	Approved
0.7731	Intermediate Similarity	NPD6616	Approved
0.7706	Intermediate Similarity	NPD6008	Approved
0.7667	Intermediate Similarity	NPD7078	Approved
0.7521	Intermediate Similarity	NPD8293	Discontinued
0.7477	Intermediate Similarity	NPD5697	Approved
0.7458	Intermediate Similarity	NPD6319	Approved
0.7456	Intermediate Similarity	NPD6882	Approved
0.7434	Intermediate Similarity	NPD4634	Approved
0.7411	Intermediate Similarity	NPD7320	Approved
0.7411	Intermediate Similarity	NPD6899	Approved
0.7411	Intermediate Similarity	NPD6881	Approved
0.7407	Intermediate Similarity	NPD5286	Approved
0.7407	Intermediate Similarity	NPD5285	Approved
0.7407	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD8035	Phase 2
0.7404	Intermediate Similarity	NPD8034	Phase 2
0.7387	Intermediate Similarity	NPD7128	Approved
0.7387	Intermediate Similarity	NPD6402	Approved
0.7387	Intermediate Similarity	NPD6675	Approved
0.7387	Intermediate Similarity	NPD5739	Approved
0.7383	Intermediate Similarity	NPD4755	Approved
0.7368	Intermediate Similarity	NPD6650	Approved
0.7368	Intermediate Similarity	NPD6649	Approved
0.735	Intermediate Similarity	NPD6009	Approved
0.7345	Intermediate Similarity	NPD6013	Approved
0.7345	Intermediate Similarity	NPD6014	Approved
0.7345	Intermediate Similarity	NPD6372	Approved
0.7345	Intermediate Similarity	NPD6012	Approved
0.7345	Intermediate Similarity	NPD6373	Approved
0.7321	Intermediate Similarity	NPD5701	Approved
0.7317	Intermediate Similarity	NPD6033	Approved
0.7281	Intermediate Similarity	NPD7102	Approved
0.7281	Intermediate Similarity	NPD6883	Approved
0.7281	Intermediate Similarity	NPD7290	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD4633	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD5224	Approved
0.7258	Intermediate Similarity	NPD7319	Approved
0.7257	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6011	Approved
0.7248	Intermediate Similarity	NPD4700	Approved
0.7241	Intermediate Similarity	NPD4632	Approved
0.7238	Intermediate Similarity	NPD6079	Approved
0.7217	Intermediate Similarity	NPD8130	Phase 1
0.7217	Intermediate Similarity	NPD6869	Approved
0.7217	Intermediate Similarity	NPD6847	Approved
0.7217	Intermediate Similarity	NPD6617	Approved
0.7212	Intermediate Similarity	NPD5328	Approved
0.7207	Intermediate Similarity	NPD5175	Approved
0.7207	Intermediate Similarity	NPD5174	Approved
0.7182	Intermediate Similarity	NPD5223	Approved
0.717	Intermediate Similarity	NPD6399	Phase 3
0.7168	Intermediate Similarity	NPD6412	Phase 2
0.7157	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8297	Approved
0.7154	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5141	Approved
0.7131	Intermediate Similarity	NPD8328	Phase 3
0.713	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5221	Approved
0.713	Intermediate Similarity	NPD5222	Approved
0.713	Intermediate Similarity	NPD4697	Phase 3
0.7129	Intermediate Similarity	NPD4788	Approved
0.7087	Intermediate Similarity	NPD3618	Phase 1
0.7064	Intermediate Similarity	NPD5173	Approved
0.7059	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3703	Phase 2
0.7009	Intermediate Similarity	NPD4202	Approved
0.7	Intermediate Similarity	NPD7638	Approved
0.6975	Remote Similarity	NPD6274	Approved
0.6967	Remote Similarity	NPD5983	Phase 2
0.6967	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5128	Approved
0.6957	Remote Similarity	NPD4730	Approved
0.6957	Remote Similarity	NPD4729	Approved
0.6949	Remote Similarity	NPD8133	Approved
0.6937	Remote Similarity	NPD7640	Approved
0.6937	Remote Similarity	NPD7639	Approved
0.693	Remote Similarity	NPD4767	Approved
0.693	Remote Similarity	NPD4768	Approved
0.6923	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7115	Discovery
0.6909	Remote Similarity	NPD7902	Approved
0.6903	Remote Similarity	NPD4754	Approved
0.6893	Remote Similarity	NPD4786	Approved
0.6863	Remote Similarity	NPD3667	Approved
0.6855	Remote Similarity	NPD6067	Discontinued
0.6855	Remote Similarity	NPD7604	Phase 2
0.6847	Remote Similarity	NPD4225	Approved
0.6838	Remote Similarity	NPD5248	Approved
0.6838	Remote Similarity	NPD5250	Approved
0.6838	Remote Similarity	NPD5247	Approved
0.6838	Remote Similarity	NPD5249	Phase 3
0.6838	Remote Similarity	NPD5251	Approved
0.6803	Remote Similarity	NPD7100	Approved
0.6803	Remote Similarity	NPD7101	Approved
0.68	Remote Similarity	NPD6697	Approved
0.68	Remote Similarity	NPD6114	Approved
0.68	Remote Similarity	NPD6115	Approved
0.68	Remote Similarity	NPD6118	Approved
0.6797	Remote Similarity	NPD5956	Approved
0.6789	Remote Similarity	NPD5282	Discontinued
0.6789	Remote Similarity	NPD7748	Approved
0.678	Remote Similarity	NPD5215	Approved
0.678	Remote Similarity	NPD5216	Approved
0.678	Remote Similarity	NPD5217	Approved
0.6777	Remote Similarity	NPD6317	Approved
0.6759	Remote Similarity	NPD7515	Phase 2
0.6757	Remote Similarity	NPD6083	Phase 2
0.6757	Remote Similarity	NPD6084	Phase 2
0.6752	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6336	Discontinued
0.6731	Remote Similarity	NPD3665	Phase 1
0.6731	Remote Similarity	NPD3666	Approved
0.6731	Remote Similarity	NPD3133	Approved
0.6729	Remote Similarity	NPD4753	Phase 2
0.6727	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5210	Approved
0.6727	Remote Similarity	NPD4629	Approved
0.6727	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1700	Approved
0.6721	Remote Similarity	NPD6313	Approved
0.6721	Remote Similarity	NPD6314	Approved
0.6721	Remote Similarity	NPD7327	Approved
0.6721	Remote Similarity	NPD7328	Approved
0.6721	Remote Similarity	NPD6335	Approved
0.67	Remote Similarity	NPD6116	Phase 1
0.6696	Remote Similarity	NPD5696	Approved
0.6695	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5135	Approved
0.6695	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD6686	Approved
0.6639	Remote Similarity	NPD5127	Approved
0.6636	Remote Similarity	NPD7900	Approved
0.6636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6411	Approved
0.66	Remote Similarity	NPD6117	Approved
0.6583	Remote Similarity	NPD6053	Discontinued
0.6577	Remote Similarity	NPD5695	Phase 3
0.6567	Remote Similarity	NPD6334	Approved
0.6567	Remote Similarity	NPD6333	Approved
0.656	Remote Similarity	NPD8033	Approved
0.656	Remote Similarity	NPD6921	Approved
0.656	Remote Similarity	NPD6909	Approved
0.656	Remote Similarity	NPD6908	Approved
0.6557	Remote Similarity	NPD6868	Approved
0.6555	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5168	Approved
0.6522	Remote Similarity	NPD7632	Discontinued
0.6505	Remote Similarity	NPD7525	Registered
0.6495	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6001	Approved
0.6481	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6903	Approved
0.648	Remote Similarity	NPD8377	Approved
0.648	Remote Similarity	NPD8294	Approved
0.6475	Remote Similarity	NPD5167	Approved
0.6449	Remote Similarity	NPD6409	Approved
0.6449	Remote Similarity	NPD7334	Approved
0.6449	Remote Similarity	NPD5330	Approved
0.6449	Remote Similarity	NPD6684	Approved
0.6449	Remote Similarity	NPD7146	Approved
0.6449	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD8378	Approved
0.6429	Remote Similarity	NPD8296	Approved
0.6429	Remote Similarity	NPD8380	Approved
0.6429	Remote Similarity	NPD8335	Approved
0.6429	Remote Similarity	NPD8379	Approved
0.6422	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6101	Approved
0.6415	Remote Similarity	NPD3668	Phase 3
0.64	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5779	Approved
0.6396	Remote Similarity	NPD5778	Approved
0.6389	Remote Similarity	NPD3573	Approved
0.6381	Remote Similarity	NPD4223	Phase 3
0.6381	Remote Similarity	NPD4221	Approved
0.633	Remote Similarity	NPD6672	Approved
0.633	Remote Similarity	NPD5737	Approved
0.6327	Remote Similarity	NPD3698	Phase 2
0.6306	Remote Similarity	NPD5284	Approved
0.6306	Remote Similarity	NPD7637	Suspended

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