NPASS Compound

Structure

NPC473360 OpenBabel07101718332D 31 34 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9016 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4839 -2.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1650 -1.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9839 0.6817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3084 -3.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8907 -3.1341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1595 -0.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9785 0.7862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4894 -2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5772 -0.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3029 -3.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5662 -0.0228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7096 -4.8566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5608 0.0817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 -1.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 1.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 14 2 0 0 0 0 2 8 2 0 0 0 0 2 14 1 0 0 0 0 3 9 1 0 0 0 0 3 15 2 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 1 0 0 0 0 5 16 2 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 25 1 0 0 0 0 20 29 2 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 31 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	417.12
Volume:	421.535
LogP:	3.242
LogD:	2.648
LogS:	-4.343
# Rotatable Bonds:	5
TPSA:	123.15
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	2.588
Fsp3:	0.042
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.913
MDCK Permeability:	9.158280590781942e-06
Pgp-inhibitor:	0.298
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	99.58641815185547%
Volume Distribution (VD):	0.396
Pgp-substrate:	1.2502464056015015%

ADMET: Metabolism

CYP1A2-inhibitor:	0.691
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.396
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.401
CYP2D6-substrate:	0.382
CYP3A4-inhibitor:	0.351
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	9.414
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.173
Rat Oral Acute Toxicity:	0.753
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.111
Carcinogencity:	0.345
Eye Corrosion:	0.003
Eye Irritation:	0.149
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC473360

Natural Product ID:	NPC473360
*Common Name:**	5-Hydroxyneolamellarin B
IUPAC Name:	2-hydroxy-3,4-bis(4-hydroxyphenyl)-1-[2-(4-hydroxyphenyl)acetyl]-2H-pyrrol-5-one
Synonyms:	5-Hydroxyneolamellarin B
Standard InCHIKey:	LUQBILKGXBTLRV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H19NO6/c26-17-7-1-14(2-8-17)13-20(29)25-23(30)21(15-3-9-18(27)10-4-15)22(24(25)31)16-5-11-19(28)12-6-16/h1-12,23,26-28,30H,13H2
SMILES:	Oc1ccc(cc1)CC(=O)N1C(=O)C(=C(C1O)c1ccc(cc1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402914
PubChem CID:	24179370
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO33428	dendrilla nigra	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17958397]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	<	20.0	%	PMID[477109]
NPT2	Others	Unspecified		Inhibition	=	22.0	%	PMID[477109]
NPT2	Others	Unspecified		Activity	=	33.0	%	PMID[477109]

☑ 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 NPC473360 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	188
0.1-0.2	1096
0.2-0.3	4826
0.3-0.4	12586
0.4-0.5	6266
0.5-0.6	14648
0.6-0.7	2958
0.7-0.8	123
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC120251
0.8321	Intermediate Similarity	NPC268348
0.8309	Intermediate Similarity	NPC257390
0.8286	Intermediate Similarity	NPC150712
0.8015	Intermediate Similarity	NPC218323
0.7868	Intermediate Similarity	NPC171372
0.7801	Intermediate Similarity	NPC266425
0.7785	Intermediate Similarity	NPC233702
0.773	Intermediate Similarity	NPC328070
0.7724	Intermediate Similarity	NPC251439
0.7676	Intermediate Similarity	NPC132308
0.7638	Intermediate Similarity	NPC70843
0.7635	Intermediate Similarity	NPC16188
0.7626	Intermediate Similarity	NPC305717
0.7594	Intermediate Similarity	NPC128249
0.7586	Intermediate Similarity	NPC471201
0.7576	Intermediate Similarity	NPC285350
0.7538	Intermediate Similarity	NPC21162
0.7536	Intermediate Similarity	NPC307020
0.7531	Intermediate Similarity	NPC256935
0.7517	Intermediate Similarity	NPC473052
0.7517	Intermediate Similarity	NPC242159
0.7517	Intermediate Similarity	NPC313694
0.7517	Intermediate Similarity	NPC473055
0.75	Intermediate Similarity	NPC95178
0.75	Intermediate Similarity	NPC29989
0.75	Intermediate Similarity	NPC69332
0.7483	Intermediate Similarity	NPC244866
0.7481	Intermediate Similarity	NPC177576
0.7466	Intermediate Similarity	NPC322526
0.7462	Intermediate Similarity	NPC88141
0.7448	Intermediate Similarity	NPC109580
0.7448	Intermediate Similarity	NPC196708
0.7447	Intermediate Similarity	NPC17374
0.7431	Intermediate Similarity	NPC169766
0.741	Intermediate Similarity	NPC285394
0.7405	Intermediate Similarity	NPC321252
0.7405	Intermediate Similarity	NPC252544
0.7394	Intermediate Similarity	NPC73555
0.7388	Intermediate Similarity	NPC23402
0.7386	Intermediate Similarity	NPC202198
0.7368	Intermediate Similarity	NPC473491
0.7364	Intermediate Similarity	NPC188677
0.7353	Intermediate Similarity	NPC249435
0.7347	Intermediate Similarity	NPC238412
0.7344	Intermediate Similarity	NPC261573
0.7344	Intermediate Similarity	NPC8931
0.7344	Intermediate Similarity	NPC120693
0.7333	Intermediate Similarity	NPC473804
0.731	Intermediate Similarity	NPC474473
0.7301	Intermediate Similarity	NPC136797
0.7297	Intermediate Similarity	NPC476989
0.7292	Intermediate Similarity	NPC45191
0.7285	Intermediate Similarity	NPC119569
0.7284	Intermediate Similarity	NPC89831
0.7273	Intermediate Similarity	NPC325651
0.7273	Intermediate Similarity	NPC116842
0.7266	Intermediate Similarity	NPC474862
0.7252	Intermediate Similarity	NPC24101
0.7252	Intermediate Similarity	NPC96224
0.7244	Intermediate Similarity	NPC155847
0.7244	Intermediate Similarity	NPC289381
0.7237	Intermediate Similarity	NPC9373
0.7226	Intermediate Similarity	NPC471033
0.7226	Intermediate Similarity	NPC311091
0.7205	Intermediate Similarity	NPC328649
0.7205	Intermediate Similarity	NPC141957
0.7195	Intermediate Similarity	NPC155506
0.7195	Intermediate Similarity	NPC159767
0.7188	Intermediate Similarity	NPC63931
0.7188	Intermediate Similarity	NPC223207
0.7181	Intermediate Similarity	NPC231572
0.7179	Intermediate Similarity	NPC476268
0.7174	Intermediate Similarity	NPC319950
0.7161	Intermediate Similarity	NPC262166
0.7153	Intermediate Similarity	NPC311737
0.7153	Intermediate Similarity	NPC38458
0.7143	Intermediate Similarity	NPC474787
0.7143	Intermediate Similarity	NPC118099
0.7143	Intermediate Similarity	NPC142577
0.7143	Intermediate Similarity	NPC474811
0.7143	Intermediate Similarity	NPC49577
0.7143	Intermediate Similarity	NPC474855
0.7143	Intermediate Similarity	NPC79465
0.7143	Intermediate Similarity	NPC76785
0.7143	Intermediate Similarity	NPC90194
0.7143	Intermediate Similarity	NPC151706
0.7143	Intermediate Similarity	NPC290755
0.7143	Intermediate Similarity	NPC476102
0.7143	Intermediate Similarity	NPC9687
0.7143	Intermediate Similarity	NPC273907
0.7143	Intermediate Similarity	NPC304074
0.7143	Intermediate Similarity	NPC293377
0.7143	Intermediate Similarity	NPC260045
0.7143	Intermediate Similarity	NPC471771
0.7143	Intermediate Similarity	NPC475598
0.7143	Intermediate Similarity	NPC475318
0.7134	Intermediate Similarity	NPC137627
0.7133	Intermediate Similarity	NPC476353
0.7132	Intermediate Similarity	NPC68269
0.7132	Intermediate Similarity	NPC160179
0.7132	Intermediate Similarity	NPC322197
0.7125	Intermediate Similarity	NPC191863
0.7125	Intermediate Similarity	NPC289776
0.7125	Intermediate Similarity	NPC133470
0.7123	Intermediate Similarity	NPC313663
0.7121	Intermediate Similarity	NPC317305
0.7121	Intermediate Similarity	NPC17525
0.7121	Intermediate Similarity	NPC153690
0.7113	Intermediate Similarity	NPC288945
0.7105	Intermediate Similarity	NPC81026
0.7092	Intermediate Similarity	NPC86900
0.709	Intermediate Similarity	NPC114682
0.709	Intermediate Similarity	NPC212718
0.7083	Intermediate Similarity	NPC165726
0.7083	Intermediate Similarity	NPC296712
0.7083	Intermediate Similarity	NPC213969
0.708	Intermediate Similarity	NPC281686
0.708	Intermediate Similarity	NPC19290
0.708	Intermediate Similarity	NPC299252
0.708	Intermediate Similarity	NPC82963
0.708	Intermediate Similarity	NPC61062
0.708	Intermediate Similarity	NPC277394
0.708	Intermediate Similarity	NPC188867
0.708	Intermediate Similarity	NPC106551
0.7073	Intermediate Similarity	NPC230611
0.7071	Intermediate Similarity	NPC56634
0.7066	Intermediate Similarity	NPC119652
0.7066	Intermediate Similarity	NPC97526
0.7063	Intermediate Similarity	NPC241794
0.7059	Intermediate Similarity	NPC125852
0.7055	Intermediate Similarity	NPC280022
0.7054	Intermediate Similarity	NPC40258
0.7054	Intermediate Similarity	NPC91461
0.7054	Intermediate Similarity	NPC7686
0.705	Intermediate Similarity	NPC182240
0.7047	Intermediate Similarity	NPC106606
0.7047	Intermediate Similarity	NPC307682
0.7045	Intermediate Similarity	NPC141523
0.7044	Intermediate Similarity	NPC244336
0.7042	Intermediate Similarity	NPC14141
0.7039	Intermediate Similarity	NPC266741
0.7037	Intermediate Similarity	NPC17693
0.7034	Intermediate Similarity	NPC478147
0.7031	Intermediate Similarity	NPC51333
0.7031	Intermediate Similarity	NPC130193
0.7031	Intermediate Similarity	NPC280869
0.7031	Intermediate Similarity	NPC216468
0.7031	Intermediate Similarity	NPC78119
0.7031	Intermediate Similarity	NPC132078
0.703	Intermediate Similarity	NPC306804
0.7024	Intermediate Similarity	NPC271792
0.7021	Intermediate Similarity	NPC27581
0.7015	Intermediate Similarity	NPC183700
0.7007	Intermediate Similarity	NPC213
0.7007	Intermediate Similarity	NPC10286
0.7006	Intermediate Similarity	NPC39431
0.7	Intermediate Similarity	NPC469243
0.7	Intermediate Similarity	NPC34634
0.7	Intermediate Similarity	NPC265454
0.7	Intermediate Similarity	NPC135784
0.7	Intermediate Similarity	NPC473136
0.6994	Remote Similarity	NPC107938
0.6994	Remote Similarity	NPC302597
0.6994	Remote Similarity	NPC294516
0.6993	Remote Similarity	NPC297322
0.6992	Remote Similarity	NPC31274
0.6988	Remote Similarity	NPC26108
0.6988	Remote Similarity	NPC279871
0.6988	Remote Similarity	NPC473402
0.6987	Remote Similarity	NPC144691
0.698	Remote Similarity	NPC6913
0.6978	Remote Similarity	NPC184527
0.6977	Remote Similarity	NPC52472
0.6977	Remote Similarity	NPC213730
0.697	Remote Similarity	NPC231705
0.6968	Remote Similarity	NPC2672
0.6966	Remote Similarity	NPC469666
0.6966	Remote Similarity	NPC81092
0.6966	Remote Similarity	NPC103605
0.6963	Remote Similarity	NPC268388
0.6962	Remote Similarity	NPC123011
0.6962	Remote Similarity	NPC256689
0.6953	Remote Similarity	NPC260000
0.6953	Remote Similarity	NPC201967
0.695	Remote Similarity	NPC236520
0.695	Remote Similarity	NPC216216
0.695	Remote Similarity	NPC294361
0.6944	Remote Similarity	NPC137416
0.694	Remote Similarity	NPC65855
0.694	Remote Similarity	NPC95172
0.694	Remote Similarity	NPC326187
0.694	Remote Similarity	NPC290566
0.694	Remote Similarity	NPC79543
0.694	Remote Similarity	NPC258056
0.694	Remote Similarity	NPC145638
0.694	Remote Similarity	NPC292758
0.6939	Remote Similarity	NPC326966
0.6937	Remote Similarity	NPC287757
0.6937	Remote Similarity	NPC319320

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 NPC473360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	592
0.2-0.3	937
0.3-0.4	1712
0.4-0.5	2743
0.5-0.6	2297
0.6-0.7	697
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7877	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD4659	Approved
0.7429	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4103	Phase 2
0.7426	Intermediate Similarity	NPD4093	Discontinued
0.7421	Intermediate Similarity	NPD5823	Approved
0.7415	Intermediate Similarity	NPD7450	Phase 2
0.741	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5157	Phase 1
0.741	Intermediate Similarity	NPD5159	Phase 2
0.7394	Intermediate Similarity	NPD4207	Discontinued
0.7389	Intermediate Similarity	NPD5967	Approved
0.7383	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2234	Approved
0.7368	Intermediate Similarity	NPD2229	Approved
0.7368	Intermediate Similarity	NPD2228	Approved
0.7338	Intermediate Similarity	NPD2562	Approved
0.7338	Intermediate Similarity	NPD2561	Approved
0.7286	Intermediate Similarity	NPD1755	Approved
0.7273	Intermediate Similarity	NPD7131	Phase 3
0.7273	Intermediate Similarity	NPD1670	Discontinued
0.7203	Intermediate Similarity	NPD4208	Discontinued
0.7197	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD743	Approved
0.7161	Intermediate Similarity	NPD7427	Discontinued
0.7153	Intermediate Similarity	NPD856	Approved
0.7153	Intermediate Similarity	NPD16	Approved
0.7152	Intermediate Similarity	NPD7577	Discontinued
0.7152	Intermediate Similarity	NPD7011	Discontinued
0.7143	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7714	Approved
0.7123	Intermediate Similarity	NPD7715	Approved
0.7103	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5303	Approved
0.7101	Intermediate Similarity	NPD5304	Approved
0.7086	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9568	Approved
0.7075	Intermediate Similarity	NPD3142	Approved
0.7075	Intermediate Similarity	NPD3140	Approved
0.7073	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5137	Approved
0.707	Intermediate Similarity	NPD3229	Phase 2
0.7066	Intermediate Similarity	NPD7695	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7177	Discontinued
0.7045	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6583	Phase 3
0.7042	Intermediate Similarity	NPD6582	Phase 2
0.7032	Intermediate Similarity	NPD5556	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7086	Phase 2
0.7007	Intermediate Similarity	NPD6405	Approved
0.7007	Intermediate Similarity	NPD6407	Approved
0.7006	Intermediate Similarity	NPD6020	Phase 2
0.6993	Remote Similarity	NPD3400	Discontinued
0.6988	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3136	Phase 2
0.6978	Remote Similarity	NPD1759	Phase 1
0.6968	Remote Similarity	NPD8165	Discontinued
0.6962	Remote Similarity	NPD824	Approved
0.6959	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3062	Approved
0.6959	Remote Similarity	NPD3061	Approved
0.6959	Remote Similarity	NPD3059	Approved
0.6957	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.694	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1792	Phase 2
0.6933	Remote Similarity	NPD7230	Approved
0.6933	Remote Similarity	NPD7231	Approved
0.6918	Remote Similarity	NPD3595	Approved
0.6918	Remote Similarity	NPD3594	Approved
0.6906	Remote Similarity	NPD317	Approved
0.6906	Remote Similarity	NPD318	Approved
0.6906	Remote Similarity	NPD1758	Phase 1
0.6897	Remote Similarity	NPD6584	Phase 3
0.6897	Remote Similarity	NPD7451	Discontinued
0.6897	Remote Similarity	NPD4980	Approved
0.6889	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD255	Approved
0.6884	Remote Similarity	NPD256	Approved
0.6879	Remote Similarity	NPD2667	Approved
0.6879	Remote Similarity	NPD2668	Approved
0.6875	Remote Similarity	NPD7110	Phase 1
0.6875	Remote Similarity	NPD6792	Phase 3
0.6875	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5311	Approved
0.6875	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5310	Approved
0.6875	Remote Similarity	NPD2079	Discontinued
0.6871	Remote Similarity	NPD5155	Approved
0.6871	Remote Similarity	NPD5156	Approved
0.6867	Remote Similarity	NPD2568	Approved
0.6867	Remote Similarity	NPD5314	Approved
0.6857	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.685	Remote Similarity	NPD2933	Approved
0.685	Remote Similarity	NPD2934	Approved
0.6849	Remote Similarity	NPD3637	Approved
0.6849	Remote Similarity	NPD3635	Approved
0.6849	Remote Similarity	NPD3636	Approved
0.6842	Remote Similarity	NPD4477	Approved
0.6842	Remote Similarity	NPD1444	Approved
0.6842	Remote Similarity	NPD1445	Approved
0.6842	Remote Similarity	NPD4476	Approved
0.6832	Remote Similarity	NPD6844	Discontinued
0.6832	Remote Similarity	NPD8019	Approved
0.6828	Remote Similarity	NPD2159	Approved
0.6828	Remote Similarity	NPD2628	Approved
0.6828	Remote Similarity	NPD3055	Approved
0.6828	Remote Similarity	NPD2160	Approved
0.6828	Remote Similarity	NPD2627	Approved
0.6828	Remote Similarity	NPD3053	Approved
0.6828	Remote Similarity	NPD2626	Approved
0.6828	Remote Similarity	NPD2625	Approved
0.6824	Remote Similarity	NPD5445	Approved
0.6824	Remote Similarity	NPD3764	Approved
0.6803	Remote Similarity	NPD2606	Approved
0.6803	Remote Similarity	NPD5203	Approved
0.6803	Remote Similarity	NPD4620	Approved
0.6803	Remote Similarity	NPD4617	Approved
0.6803	Remote Similarity	NPD2605	Approved
0.6803	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5201	Approved
0.6797	Remote Similarity	NPD2859	Approved
0.6797	Remote Similarity	NPD2860	Approved
0.6797	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD520	Approved
0.6774	Remote Similarity	NPD5481	Discontinued
0.6772	Remote Similarity	NPD7303	Discontinued
0.6768	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1751	Approved
0.6761	Remote Similarity	NPD3019	Approved
0.6757	Remote Similarity	NPD5163	Phase 2
0.6755	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3052	Approved
0.6755	Remote Similarity	NPD3054	Approved
0.6753	Remote Similarity	NPD7037	Approved
0.6753	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3455	Phase 2
0.6746	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7693	Approved
0.6742	Remote Similarity	NPD4658	Approved
0.6742	Remote Similarity	NPD4656	Approved
0.6738	Remote Similarity	NPD316	Approved
0.6735	Remote Similarity	NPD5204	Approved
0.6733	Remote Similarity	NPD6346	Approved
0.6733	Remote Similarity	NPD6309	Approved
0.6733	Remote Similarity	NPD6311	Approved
0.6733	Remote Similarity	NPD6310	Approved
0.6731	Remote Similarity	NPD8131	Suspended
0.673	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3123	Discovery
0.6713	Remote Similarity	NPD4136	Approved
0.6713	Remote Similarity	NPD4106	Approved
0.6713	Remote Similarity	NPD4135	Approved
0.6713	Remote Similarity	NPD3421	Phase 3
0.6712	Remote Similarity	NPD1133	Approved
0.6712	Remote Similarity	NPD1134	Approved
0.6712	Remote Similarity	NPD1135	Approved
0.6712	Remote Similarity	NPD1131	Approved
0.6712	Remote Similarity	NPD1129	Approved
0.6711	Remote Similarity	NPD3555	Approved
0.6711	Remote Similarity	NPD3554	Approved
0.6711	Remote Similarity	NPD4619	Approved
0.6711	Remote Similarity	NPD4621	Approved
0.6711	Remote Similarity	NPD3552	Approved
0.6711	Remote Similarity	NPD3553	Approved
0.6708	Remote Similarity	NPD6502	Phase 2
0.6708	Remote Similarity	NPD6876	Approved
0.6708	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6875	Approved
0.6707	Remote Similarity	NPD6747	Phase 1
0.6707	Remote Similarity	NPD7608	Discontinued
0.6692	Remote Similarity	NPD9608	Approved
0.6692	Remote Similarity	NPD9610	Approved
0.6691	Remote Similarity	NPD1793	Approved
0.6691	Remote Similarity	NPD1791	Approved
0.6689	Remote Similarity	NPD2614	Approved
0.6688	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7039	Approved
0.6686	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7038	Approved
0.6667	Remote Similarity	NPD9616	Approved
0.6667	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9613	Approved
0.6667	Remote Similarity	NPD7018	Phase 2
0.6667	Remote Similarity	NPD855	Approved
0.6667	Remote Similarity	NPD6386	Approved
0.6667	Remote Similarity	NPD6385	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