NPASS Compound

Structure

NPC329837 OpenBabel07101719132D 28 30 0 0 1 0 0 0 0 0999 V2000 -3.0712 -3.8064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0751 0.6323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9248 -0.6676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6300 0.2880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3854 1.6886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9487 -2.5149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6110 0.6323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9459 -2.5896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4771 1.1323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5895 -1.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8042 -3.1262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3854 -1.6886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6110 -0.3677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6261 -1.8565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3431 0.6323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2697 -1.1781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 -0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4771 -0.8677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3431 -0.3677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5817 -2.1513 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7598 -3.4210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2091 -0.8677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2091 1.1323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2446 -1.4006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6551 0.5105 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2948 0.9556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 22 2 3 0 0 0 11 23 1 0 0 0 0 12 17 1 0 0 0 0 13 17 1 0 0 0 0 13 18 2 0 0 0 0 14 18 1 0 0 0 0 14 22 1 6 0 0 0 15 19 2 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 16 26 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	387.17
Volume:	391.386
LogP:	1.672
LogD:	1.919
LogS:	-3.082
# Rotatable Bonds:	6
TPSA:	86.25
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.819
Synthetic Accessibility Score:	3.001
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825
MDCK Permeability:	1.9156250345986336e-05
Pgp-inhibitor:	0.434
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	78.48018646240234%
Volume Distribution (VD):	0.676
Pgp-substrate:	16.393123626708984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.547
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.886

ADMET: Excretion

Clearance (CL):	2.64
Half-life (T1/2):	0.592

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.758
Drug-inuced Liver Injury (DILI):	0.087
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.11
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC329837

Natural Product ID:	NPC329837
*Common Name:**	(-)-Androbiphenyline
IUPAC Name:	N-[(7S)-8-hydroxy-1,2,3,9-tetramethoxy-6,7-dihydro-5H-dibenzo[5,3-b:2',4'-e][7]annulen-7-yl]acetamide
Synonyms:	(-)-Androbiphenyline
Standard InCHIKey:	DMFNBXZGZQLZMS-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C21H25NO6/c1-11(23)22-14-8-6-12-10-16(26-3)20(27-4)21(28-5)17(12)13-7-9-15(25-2)19(24)18(13)14/h7,9-10,14,24H,6,8H2,1-5H3,(H,22,23)/t14-/m0/s1
SMILES:	CC(=O)NC1CCC2=CC(=C(C(=C2C3=C1C(=C(C=C3)OC)O)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498122
PubChem CID:	10927179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003776] Allocolchicine alkaloids

*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
NPO24146	Colchicum brachyphyllum	Species	Colchicaceae	Eukaryota	n.a.	Jordanian	n.a.	PMID[15730238]
NPO24146	Colchicum brachyphyllum	Species	Colchicaceae	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
EC50	3
MIC	4
Others	3

Activity Type	# Activity
Cell Line	3
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	200.0	nM	PMID[570101]
NPT397	Cell Line	NCI-H460	Homo sapiens	EC50	=	260.0	nM	PMID[570101]
NPT395	Cell Line	SF-268	Homo sapiens	EC50	=	370.0	nM	PMID[570101]
NPT140	Organism	Artemia	Artemia	LC50	=	48.8	ug.mL-1	PMID[570101]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	500.0	ug.mL-1	PMID[570101]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	500.0	ug.mL-1	PMID[570101]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	500.0	ug.mL-1	PMID[570101]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	500.0	ug.mL-1	PMID[570101]
NPT2	Others	Unspecified		Activity	=	50.0	%	PMID[570101]

☑ 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 NPC329837 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	289
0.1-0.2	1441
0.2-0.3	7598
0.3-0.4	10736
0.4-0.5	5122
0.5-0.6	8401
0.6-0.7	6950
0.7-0.8	1873
0.8-0.85	255
0.85-0.9	26
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8944	High Similarity	NPC231371
0.882	High Similarity	NPC204908
0.882	High Similarity	NPC83198
0.8812	High Similarity	NPC264850
0.8812	High Similarity	NPC13916
0.875	High Similarity	NPC24465
0.8696	High Similarity	NPC68328
0.8679	High Similarity	NPC202839
0.8679	High Similarity	NPC66678
0.8659	High Similarity	NPC190783
0.8659	High Similarity	NPC232386
0.8659	High Similarity	NPC152680
0.8658	High Similarity	NPC296898
0.8654	High Similarity	NPC275027
0.8485	Intermediate Similarity	NPC239775
0.8471	Intermediate Similarity	NPC127402
0.8424	Intermediate Similarity	NPC118274
0.8424	Intermediate Similarity	NPC168753
0.8389	Intermediate Similarity	NPC32778
0.8365	Intermediate Similarity	NPC108957
0.8365	Intermediate Similarity	NPC226941
0.8365	Intermediate Similarity	NPC14005
0.8365	Intermediate Similarity	NPC475557
0.8344	Intermediate Similarity	NPC477565
0.8344	Intermediate Similarity	NPC103379
0.8343	Intermediate Similarity	NPC474507
0.8313	Intermediate Similarity	NPC204828
0.8313	Intermediate Similarity	NPC127674
0.8313	Intermediate Similarity	NPC184026
0.8313	Intermediate Similarity	NPC249797
0.8313	Intermediate Similarity	NPC295691
0.8313	Intermediate Similarity	NPC276588
0.8313	Intermediate Similarity	NPC107602
0.8313	Intermediate Similarity	NPC207757
0.8313	Intermediate Similarity	NPC278799
0.8313	Intermediate Similarity	NPC5238
0.8313	Intermediate Similarity	NPC469817
0.8313	Intermediate Similarity	NPC39701
0.8313	Intermediate Similarity	NPC172765
0.8313	Intermediate Similarity	NPC110416
0.8313	Intermediate Similarity	NPC189266
0.8313	Intermediate Similarity	NPC193949
0.8313	Intermediate Similarity	NPC54379
0.8313	Intermediate Similarity	NPC2413
0.8311	Intermediate Similarity	NPC126836
0.8286	Intermediate Similarity	NPC85381
0.828	Intermediate Similarity	NPC476571
0.828	Intermediate Similarity	NPC147390
0.828	Intermediate Similarity	NPC428
0.828	Intermediate Similarity	NPC135538
0.828	Intermediate Similarity	NPC246587
0.828	Intermediate Similarity	NPC24233
0.8276	Intermediate Similarity	NPC41122
0.8276	Intermediate Similarity	NPC318805
0.8267	Intermediate Similarity	NPC218530
0.8255	Intermediate Similarity	NPC130595
0.8255	Intermediate Similarity	NPC214869
0.8255	Intermediate Similarity	NPC93882
0.8246	Intermediate Similarity	NPC217748
0.8246	Intermediate Similarity	NPC258657
0.8246	Intermediate Similarity	NPC49075
0.8246	Intermediate Similarity	NPC279228
0.8246	Intermediate Similarity	NPC90998
0.8246	Intermediate Similarity	NPC328155
0.8246	Intermediate Similarity	NPC15414
0.8246	Intermediate Similarity	NPC7715
0.8246	Intermediate Similarity	NPC8836
0.8246	Intermediate Similarity	NPC229373
0.8246	Intermediate Similarity	NPC182052
0.8246	Intermediate Similarity	NPC239824
0.8246	Intermediate Similarity	NPC251735
0.8246	Intermediate Similarity	NPC54654
0.8246	Intermediate Similarity	NPC290005
0.8246	Intermediate Similarity	NPC290582
0.8246	Intermediate Similarity	NPC181796
0.8246	Intermediate Similarity	NPC285931
0.8246	Intermediate Similarity	NPC223690
0.8246	Intermediate Similarity	NPC185639
0.8246	Intermediate Similarity	NPC104196
0.8246	Intermediate Similarity	NPC42663
0.8246	Intermediate Similarity	NPC271013
0.8246	Intermediate Similarity	NPC222661
0.8246	Intermediate Similarity	NPC311973
0.8225	Intermediate Similarity	NPC148709
0.8225	Intermediate Similarity	NPC476577
0.8225	Intermediate Similarity	NPC173416
0.8217	Intermediate Similarity	NPC321505
0.8217	Intermediate Similarity	NPC191376
0.8217	Intermediate Similarity	NPC179825
0.8217	Intermediate Similarity	NPC476151
0.821	Intermediate Similarity	NPC195766
0.821	Intermediate Similarity	NPC206736
0.82	Intermediate Similarity	NPC313737
0.82	Intermediate Similarity	NPC6854
0.82	Intermediate Similarity	NPC285078
0.8198	Intermediate Similarity	NPC274716
0.8198	Intermediate Similarity	NPC254441
0.8198	Intermediate Similarity	NPC167116
0.8193	Intermediate Similarity	NPC205421
0.8193	Intermediate Similarity	NPC117188
0.8193	Intermediate Similarity	NPC12053
0.8193	Intermediate Similarity	NPC474931
0.8193	Intermediate Similarity	NPC306555
0.8193	Intermediate Similarity	NPC81218
0.8193	Intermediate Similarity	NPC158376
0.8193	Intermediate Similarity	NPC145832
0.8192	Intermediate Similarity	NPC234318
0.8188	Intermediate Similarity	NPC114102
0.8187	Intermediate Similarity	NPC286119
0.8182	Intermediate Similarity	NPC253043
0.8182	Intermediate Similarity	NPC477563
0.8182	Intermediate Similarity	NPC306843
0.8182	Intermediate Similarity	NPC196447
0.8182	Intermediate Similarity	NPC78222
0.8182	Intermediate Similarity	NPC212794
0.8182	Intermediate Similarity	NPC136508
0.8182	Intermediate Similarity	NPC13504
0.8182	Intermediate Similarity	NPC96603
0.8176	Intermediate Similarity	NPC154866
0.8171	Intermediate Similarity	NPC60186
0.817	Intermediate Similarity	NPC299583
0.8161	Intermediate Similarity	NPC275680
0.8161	Intermediate Similarity	NPC22115
0.8158	Intermediate Similarity	NPC294884
0.8158	Intermediate Similarity	NPC158142
0.8158	Intermediate Similarity	NPC69029
0.8158	Intermediate Similarity	NPC10314
0.8158	Intermediate Similarity	NPC200557
0.8158	Intermediate Similarity	NPC108198
0.8144	Intermediate Similarity	NPC182257
0.814	Intermediate Similarity	NPC30779
0.8137	Intermediate Similarity	NPC2295
0.8137	Intermediate Similarity	NPC44642
0.8137	Intermediate Similarity	NPC477564
0.8125	Intermediate Similarity	NPC52475
0.8121	Intermediate Similarity	NPC324144
0.8121	Intermediate Similarity	NPC35961
0.8121	Intermediate Similarity	NPC195749
0.8121	Intermediate Similarity	NPC52029
0.8114	Intermediate Similarity	NPC206900
0.811	Intermediate Similarity	NPC119649
0.811	Intermediate Similarity	NPC235143
0.811	Intermediate Similarity	NPC230956
0.811	Intermediate Similarity	NPC271388
0.811	Intermediate Similarity	NPC205255
0.8108	Intermediate Similarity	NPC159968
0.8108	Intermediate Similarity	NPC74817
0.8108	Intermediate Similarity	NPC246620
0.8108	Intermediate Similarity	NPC266555
0.8108	Intermediate Similarity	NPC124452
0.8108	Intermediate Similarity	NPC293054
0.8108	Intermediate Similarity	NPC236791
0.8108	Intermediate Similarity	NPC82679
0.8108	Intermediate Similarity	NPC324112
0.8108	Intermediate Similarity	NPC282000
0.8108	Intermediate Similarity	NPC169474
0.8107	Intermediate Similarity	NPC474051
0.8107	Intermediate Similarity	NPC228040
0.8105	Intermediate Similarity	NPC41473
0.8105	Intermediate Similarity	NPC143139
0.8105	Intermediate Similarity	NPC312770
0.8105	Intermediate Similarity	NPC14600
0.8105	Intermediate Similarity	NPC204848
0.8105	Intermediate Similarity	NPC160607
0.8105	Intermediate Similarity	NPC202846
0.8103	Intermediate Similarity	NPC116465
0.8103	Intermediate Similarity	NPC212237
0.8092	Intermediate Similarity	NPC276026
0.8092	Intermediate Similarity	NPC289258
0.8092	Intermediate Similarity	NPC555
0.8092	Intermediate Similarity	NPC469659
0.8092	Intermediate Similarity	NPC7515
0.8092	Intermediate Similarity	NPC188378
0.8092	Intermediate Similarity	NPC206737
0.8092	Intermediate Similarity	NPC56764
0.8092	Intermediate Similarity	NPC125649
0.8089	Intermediate Similarity	NPC5462
0.8089	Intermediate Similarity	NPC185838
0.8075	Intermediate Similarity	NPC18614
0.8067	Intermediate Similarity	NPC255550
0.8067	Intermediate Similarity	NPC308885
0.8063	Intermediate Similarity	NPC220858
0.8063	Intermediate Similarity	NPC97221
0.8063	Intermediate Similarity	NPC88249
0.8063	Intermediate Similarity	NPC151895
0.8063	Intermediate Similarity	NPC192768
0.8061	Intermediate Similarity	NPC79402
0.8061	Intermediate Similarity	NPC80759
0.8054	Intermediate Similarity	NPC155838
0.8052	Intermediate Similarity	NPC242715
0.8052	Intermediate Similarity	NPC56329
0.8049	Intermediate Similarity	NPC221864
0.8046	Intermediate Similarity	NPC302245
0.8046	Intermediate Similarity	NPC95426
0.8046	Intermediate Similarity	NPC16357
0.8041	Intermediate Similarity	NPC44748
0.8041	Intermediate Similarity	NPC28730
0.8041	Intermediate Similarity	NPC18924
0.8041	Intermediate Similarity	NPC103823
0.8041	Intermediate Similarity	NPC78974

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 NPC329837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	727
0.2-0.3	1167
0.3-0.4	2195
0.4-0.5	2461
0.5-0.6	1557
0.6-0.7	698
0.7-0.8	133
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9161	High Similarity	NPD4055	Discovery
0.8365	Intermediate Similarity	NPD5089	Approved
0.8365	Intermediate Similarity	NPD5090	Approved
0.8354	Intermediate Similarity	NPD4005	Discontinued
0.8255	Intermediate Similarity	NPD2674	Phase 3
0.8246	Intermediate Similarity	NPD8053	Approved
0.8246	Intermediate Similarity	NPD8054	Approved
0.811	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3145	Approved
0.8067	Intermediate Similarity	NPD3144	Approved
0.7963	Intermediate Similarity	NPD4678	Approved
0.7963	Intermediate Similarity	NPD4675	Approved
0.7875	Intermediate Similarity	NPD4584	Approved
0.7836	Intermediate Similarity	NPD8252	Approved
0.7836	Intermediate Similarity	NPD8251	Approved
0.7836	Intermediate Similarity	NPD8099	Discontinued
0.7834	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD8156	Discontinued
0.7763	Intermediate Similarity	NPD3027	Phase 3
0.7725	Intermediate Similarity	NPD6788	Approved
0.7665	Intermediate Similarity	NPD2563	Approved
0.7665	Intermediate Similarity	NPD2560	Approved
0.7654	Intermediate Similarity	NPD4123	Phase 3
0.7605	Intermediate Similarity	NPD4585	Approved
0.76	Intermediate Similarity	NPD1669	Approved
0.7598	Intermediate Similarity	NPD6841	Approved
0.7598	Intermediate Similarity	NPD6843	Phase 3
0.7598	Intermediate Similarity	NPD6842	Approved
0.7588	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7124	Phase 2
0.7516	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4010	Discontinued
0.7485	Intermediate Similarity	NPD4357	Discontinued
0.7485	Intermediate Similarity	NPD6072	Discontinued
0.747	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD5241	Discontinued
0.7468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1424	Approved
0.7438	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD27	Approved
0.7414	Intermediate Similarity	NPD2489	Approved
0.7414	Intermediate Similarity	NPD2898	Approved
0.7407	Intermediate Similarity	NPD6331	Phase 2
0.7403	Intermediate Similarity	NPD7906	Approved
0.7403	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6071	Discontinued
0.7396	Intermediate Similarity	NPD5773	Approved
0.7396	Intermediate Similarity	NPD5772	Approved
0.7394	Intermediate Similarity	NPD52	Approved
0.7394	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7526	Approved
0.7391	Intermediate Similarity	NPD7153	Discontinued
0.7389	Intermediate Similarity	NPD1613	Approved
0.7389	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2161	Phase 2
0.7362	Intermediate Similarity	NPD302	Approved
0.7356	Intermediate Similarity	NPD2970	Approved
0.7356	Intermediate Similarity	NPD2969	Approved
0.7346	Intermediate Similarity	NPD3060	Approved
0.7333	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7827	Phase 1
0.7318	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1024	Discontinued
0.7299	Intermediate Similarity	NPD3051	Approved
0.7296	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD2978	Approved
0.7294	Intermediate Similarity	NPD2977	Approved
0.7278	Intermediate Similarity	NPD4577	Approved
0.7278	Intermediate Similarity	NPD4578	Approved
0.7278	Intermediate Similarity	NPD7312	Approved
0.7278	Intermediate Similarity	NPD2238	Phase 2
0.7278	Intermediate Similarity	NPD4773	Phase 2
0.7278	Intermediate Similarity	NPD4772	Phase 2
0.7278	Intermediate Similarity	NPD7313	Approved
0.7278	Intermediate Similarity	NPD7310	Approved
0.7278	Intermediate Similarity	NPD7311	Approved
0.7273	Intermediate Similarity	NPD2420	Approved
0.7273	Intermediate Similarity	NPD2421	Approved
0.7262	Intermediate Similarity	NPD4017	Approved
0.7261	Intermediate Similarity	NPD5109	Approved
0.7261	Intermediate Similarity	NPD5111	Phase 2
0.7261	Intermediate Similarity	NPD5110	Phase 2
0.7253	Intermediate Similarity	NPD4663	Approved
0.7239	Intermediate Similarity	NPD5177	Phase 3
0.7239	Intermediate Similarity	NPD4237	Approved
0.7239	Intermediate Similarity	NPD4236	Phase 3
0.7238	Intermediate Similarity	NPD7309	Approved
0.7222	Intermediate Similarity	NPD1375	Discontinued
0.7219	Intermediate Similarity	NPD5617	Suspended
0.7215	Intermediate Similarity	NPD7477	Discontinued
0.7207	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4108	Discontinued
0.7197	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6746	Phase 2
0.7179	Intermediate Similarity	NPD3018	Phase 2
0.7175	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7833	Phase 2
0.7168	Intermediate Similarity	NPD7831	Phase 2
0.716	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2219	Phase 1
0.7143	Intermediate Similarity	NPD6030	Approved
0.7143	Intermediate Similarity	NPD6111	Discontinued
0.7143	Intermediate Similarity	NPD6031	Approved
0.7135	Intermediate Similarity	NPD7298	Approved
0.711	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3845	Phase 1
0.7107	Intermediate Similarity	NPD4475	Approved
0.7107	Intermediate Similarity	NPD839	Approved
0.7107	Intermediate Similarity	NPD4474	Approved
0.7107	Intermediate Similarity	NPD840	Approved
0.7097	Intermediate Similarity	NPD2922	Phase 1
0.7089	Intermediate Similarity	NPD4625	Phase 3
0.7078	Intermediate Similarity	NPD2232	Approved
0.7078	Intermediate Similarity	NPD2230	Approved
0.7078	Intermediate Similarity	NPD2233	Approved
0.7063	Intermediate Similarity	NPD1558	Phase 1
0.7062	Intermediate Similarity	NPD4083	Discontinued
0.7053	Intermediate Similarity	NPD8095	Phase 1
0.7053	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2677	Approved
0.7048	Intermediate Similarity	NPD3692	Discontinued
0.7041	Intermediate Similarity	NPD3641	Approved
0.7041	Intermediate Similarity	NPD3640	Phase 3
0.7041	Intermediate Similarity	NPD3639	Approved
0.7037	Intermediate Similarity	NPD6896	Approved
0.7037	Intermediate Similarity	NPD6895	Approved
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.7032	Intermediate Similarity	NPD2983	Phase 2
0.7032	Intermediate Similarity	NPD2982	Phase 2
0.7032	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4162	Approved
0.7025	Intermediate Similarity	NPD4908	Phase 1
0.7025	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4739	Approved
0.7024	Intermediate Similarity	NPD7447	Phase 1
0.7024	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3296	Phase 1
0.7	Intermediate Similarity	NPD2883	Discontinued
0.6994	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2668	Approved
0.6993	Remote Similarity	NPD2667	Approved
0.6989	Remote Similarity	NPD4666	Phase 3
0.6982	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6090	Discontinued
0.698	Remote Similarity	NPD5283	Phase 1
0.6975	Remote Similarity	NPD2157	Approved
0.6974	Remote Similarity	NPD7263	Phase 2
0.6968	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7125	Discontinued
0.6968	Remote Similarity	NPD2981	Phase 2
0.6966	Remote Similarity	NPD5242	Approved
0.6964	Remote Similarity	NPD7212	Phase 2
0.6964	Remote Similarity	NPD7213	Phase 3
0.6962	Remote Similarity	NPD1712	Approved
0.6959	Remote Similarity	NPD228	Approved
0.6946	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5005	Approved
0.6943	Remote Similarity	NPD5006	Approved
0.6943	Remote Similarity	NPD3053	Approved
0.6943	Remote Similarity	NPD3055	Approved
0.6937	Remote Similarity	NPD5718	Phase 2
0.6937	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5709	Phase 3
0.6927	Remote Similarity	NPD4481	Phase 3
0.6923	Remote Similarity	NPD7007	Discovery
0.6918	Remote Similarity	NPD600	Approved
0.6918	Remote Similarity	NPD596	Approved
0.6905	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1610	Phase 2
0.6902	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5677	Discontinued
0.6891	Remote Similarity	NPD3452	Approved
0.6891	Remote Similarity	NPD3450	Approved
0.6891	Remote Similarity	NPD2493	Approved
0.6891	Remote Similarity	NPD2494	Approved
0.689	Remote Similarity	NPD2154	Approved
0.689	Remote Similarity	NPD2155	Approved
0.689	Remote Similarity	NPD2156	Approved
0.6887	Remote Similarity	NPD709	Approved
0.6879	Remote Similarity	NPD7438	Suspended
0.6875	Remote Similarity	NPD5604	Discontinued
0.6871	Remote Similarity	NPD2568	Approved
0.6864	Remote Similarity	NPD6087	Phase 1
0.6862	Remote Similarity	NPD2488	Approved
0.6862	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD2490	Approved
0.6842	Remote Similarity	NPD2122	Discontinued
0.6842	Remote Similarity	NPD5976	Discontinued
0.6839	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1934	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