NPASS Compound

Structure

NPC472209 OpenBabel07101718332D 29 34 0 0 1 0 0 0 0 0999 V2000 2.9215 0.3230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0524 -2.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3038 2.1169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9326 0.2178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9344 0.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3081 -0.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3117 1.2994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7532 -0.0457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9744 0.2249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0555 -0.1770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9270 -2.5110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6162 -0.9378 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6854 0.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6872 0.9409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1411 0.6177 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4894 -0.6323 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0555 -0.6842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8333 -1.3870 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4218 0.5836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0872 -0.9962 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9215 -1.1842 0.0000 C 0 0 0 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 -0.0029 1.1651 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 1.6162 0.0766 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7841 -3.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9215 -2.1842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7875 -0.6842 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 1.9765 1.0094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9444 -1.5112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 11 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 12 1 0 0 0 0 10 1 1 1 0 0 0 10 17 1 0 0 0 0 10 24 1 0 0 0 0 11 25 2 0 0 0 0 11 29 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 8 1 6 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 9 1 1 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 6 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 22 1 0 0 0 0 20 29 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 9 1 1 0 0 0 24 28 2 0 0 0 0 M CHG 2 23 1 27 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.27
Volume:	565.656
LogP:	5.627
LogD:	3.127
LogS:	-3.189
# Rotatable Bonds:	10
TPSA:	144.52
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.201
Synthetic Accessibility Score:	4.465
Fsp3:	0.484
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.896
MDCK Permeability:	8.979453923529945e-06
Pgp-inhibitor:	0.779
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.447
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	97.3663558959961%
Volume Distribution (VD):	0.374
Pgp-substrate:	1.2837506532669067%

ADMET: Metabolism

CYP1A2-inhibitor:	0.322
CYP1A2-substrate:	0.647
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.423
CYP2C9-inhibitor:	0.805
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.719
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.348
CYP3A4-substrate:	0.387

ADMET: Excretion

Clearance (CL):	1.74
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.392
Drug-inuced Liver Injury (DILI):	0.415
AMES Toxicity:	0.652
Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.695
Carcinogencity:	0.085
Eye Corrosion:	0.003
Eye Irritation:	0.123
Respiratory Toxicity:	0.321

Download Data

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

Natural Product: NPC472209

Natural Product ID:	NPC472209
*Common Name:**	MVVOGBRCQSCYJN-QWWWVCEYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MVVOGBRCQSCYJN-QWWWVCEYSA-N
Standard InCHI:	InChI=1S/C22H24N2O5/c1-10-17(21(26)27)12-8-15-19-22(13-6-4-5-7-14(13)23(19)3)9-16(24(10,15)28)18(12)20(22)29-11(2)25/h4-7,10,12,15-18,20H,8-9H2,1-3H3/t10-,12?,15-,16-,17-,18?,20?,22+,24?/m0/s1
SMILES:	CC(=O)OC1C2C3C[C@H]4C5=[N+](c6c([C@@]15C[C@@H]2N4(=O)[C@H]([C@@H]3C(=O)[O-])C)cccc6)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3351040
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001794] Ajmaline-sarpagine 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
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19775092]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	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	2
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	45.03	%	PMID[536679]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	94.84	%	PMID[536679]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	<	0.0	%	PMID[536679]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[536679]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	40000.0	nM	PMID[536679]

☑ 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 NPC472209 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	292
0.1-0.2	1308
0.2-0.3	3642
0.3-0.4	20280
0.4-0.5	12498
0.5-0.6	3664
0.6-0.7	871
0.7-0.8	131
0.8-0.85	3
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC469460
0.8902	High Similarity	NPC469461
0.883	High Similarity	NPC476326
0.8571	High Similarity	NPC476428
0.848	Intermediate Similarity	NPC469462
0.8439	Intermediate Similarity	NPC476425
0.8136	Intermediate Similarity	NPC476441
0.8	Intermediate Similarity	NPC478076
0.7821	Intermediate Similarity	NPC276993
0.7821	Intermediate Similarity	NPC181138
0.7821	Intermediate Similarity	NPC21752
0.7821	Intermediate Similarity	NPC210415
0.7821	Intermediate Similarity	NPC293255
0.7821	Intermediate Similarity	NPC298851
0.7696	Intermediate Similarity	NPC475559
0.7663	Intermediate Similarity	NPC475962
0.7582	Intermediate Similarity	NPC13367
0.7543	Intermediate Similarity	NPC161827
0.7543	Intermediate Similarity	NPC473297
0.7513	Intermediate Similarity	NPC302548
0.7472	Intermediate Similarity	NPC477158
0.7472	Intermediate Similarity	NPC143457
0.7458	Intermediate Similarity	NPC153694
0.7458	Intermediate Similarity	NPC211525
0.7444	Intermediate Similarity	NPC52059
0.7444	Intermediate Similarity	NPC470069
0.7416	Intermediate Similarity	NPC310403
0.7416	Intermediate Similarity	NPC243673
0.7416	Intermediate Similarity	NPC97380
0.7416	Intermediate Similarity	NPC63210
0.7416	Intermediate Similarity	NPC263709
0.7416	Intermediate Similarity	NPC148468
0.7407	Intermediate Similarity	NPC282092
0.7341	Intermediate Similarity	NPC472100
0.7303	Intermediate Similarity	NPC29285
0.7263	Intermediate Similarity	NPC113946
0.7258	Intermediate Similarity	NPC264482
0.7258	Intermediate Similarity	NPC203202
0.7253	Intermediate Similarity	NPC472106
0.725	Intermediate Similarity	NPC475847
0.725	Intermediate Similarity	NPC185742
0.7219	Intermediate Similarity	NPC186669
0.7211	Intermediate Similarity	NPC245741
0.7188	Intermediate Similarity	NPC14994
0.7181	Intermediate Similarity	NPC6974
0.7158	Intermediate Similarity	NPC159963
0.7157	Intermediate Similarity	NPC469736
0.7143	Intermediate Similarity	NPC472121
0.7143	Intermediate Similarity	NPC474121
0.7143	Intermediate Similarity	NPC472120
0.7143	Intermediate Similarity	NPC472101
0.7136	Intermediate Similarity	NPC475489
0.7128	Intermediate Similarity	NPC260075
0.712	Intermediate Similarity	NPC278887
0.712	Intermediate Similarity	NPC472115
0.712	Intermediate Similarity	NPC472114
0.7112	Intermediate Similarity	NPC469726
0.7112	Intermediate Similarity	NPC329338
0.709	Intermediate Similarity	NPC99043
0.709	Intermediate Similarity	NPC218594
0.7089	Intermediate Similarity	NPC476436
0.7088	Intermediate Similarity	NPC225319
0.7077	Intermediate Similarity	NPC472097
0.7077	Intermediate Similarity	NPC25401
0.7049	Intermediate Similarity	NPC176983
0.7031	Intermediate Similarity	NPC472119
0.7031	Intermediate Similarity	NPC97584
0.7017	Intermediate Similarity	NPC477156
0.7017	Intermediate Similarity	NPC477157
0.6995	Remote Similarity	NPC79062
0.6995	Remote Similarity	NPC472107
0.698	Remote Similarity	NPC474077
0.6957	Remote Similarity	NPC99632
0.6957	Remote Similarity	NPC282339
0.6927	Remote Similarity	NPC476429
0.6919	Remote Similarity	NPC469541
0.6902	Remote Similarity	NPC474058
0.6893	Remote Similarity	NPC116519
0.6891	Remote Similarity	NPC472104
0.6881	Remote Similarity	NPC199851
0.6881	Remote Similarity	NPC254240
0.6881	Remote Similarity	NPC294909
0.6881	Remote Similarity	NPC312870
0.6881	Remote Similarity	NPC128265
0.6866	Remote Similarity	NPC52557
0.6865	Remote Similarity	NPC286871
0.6853	Remote Similarity	NPC473298
0.6853	Remote Similarity	NPC22689
0.6853	Remote Similarity	NPC105055
0.6837	Remote Similarity	NPC472323
0.6837	Remote Similarity	NPC181928
0.6836	Remote Similarity	NPC472103
0.6809	Remote Similarity	NPC223595
0.6809	Remote Similarity	NPC167724
0.6809	Remote Similarity	NPC224970
0.6804	Remote Similarity	NPC143533
0.6789	Remote Similarity	NPC251212
0.6789	Remote Similarity	NPC214626
0.6789	Remote Similarity	NPC139085
0.6786	Remote Similarity	NPC66210
0.6774	Remote Similarity	NPC472117
0.6769	Remote Similarity	NPC258480
0.6766	Remote Similarity	NPC245916
0.6757	Remote Similarity	NPC193410
0.6755	Remote Similarity	NPC279527
0.6755	Remote Similarity	NPC214960
0.6734	Remote Similarity	NPC28510
0.672	Remote Similarity	NPC248117
0.672	Remote Similarity	NPC201424
0.672	Remote Similarity	NPC472102
0.672	Remote Similarity	NPC309531
0.6716	Remote Similarity	NPC289299
0.6716	Remote Similarity	NPC57994
0.6716	Remote Similarity	NPC34717
0.6703	Remote Similarity	NPC61013
0.6702	Remote Similarity	NPC96901
0.6701	Remote Similarity	NPC15840
0.6683	Remote Similarity	NPC471512
0.6667	Remote Similarity	NPC203972
0.665	Remote Similarity	NPC162730
0.665	Remote Similarity	NPC90967
0.665	Remote Similarity	NPC137589
0.665	Remote Similarity	NPC52262
0.6636	Remote Similarity	NPC106593
0.6635	Remote Similarity	NPC238457
0.6633	Remote Similarity	NPC477159
0.6617	Remote Similarity	NPC472113
0.6616	Remote Similarity	NPC291759
0.6616	Remote Similarity	NPC478077
0.6606	Remote Similarity	NPC473667
0.6602	Remote Similarity	NPC469732
0.6601	Remote Similarity	NPC472116
0.66	Remote Similarity	NPC314333
0.66	Remote Similarity	NPC329858
0.66	Remote Similarity	NPC472112
0.6596	Remote Similarity	NPC293458
0.6591	Remote Similarity	NPC469720
0.6583	Remote Similarity	NPC21425
0.6578	Remote Similarity	NPC36495
0.6573	Remote Similarity	NPC472291
0.657	Remote Similarity	NPC474116
0.657	Remote Similarity	NPC1464
0.6566	Remote Similarity	NPC133591
0.6561	Remote Similarity	NPC33949
0.6546	Remote Similarity	NPC472122
0.6546	Remote Similarity	NPC24594
0.6544	Remote Similarity	NPC140311
0.6535	Remote Similarity	NPC55493
0.6533	Remote Similarity	NPC207033
0.6533	Remote Similarity	NPC38823
0.6532	Remote Similarity	NPC223242
0.6531	Remote Similarity	NPC472105
0.6531	Remote Similarity	NPC187827
0.6528	Remote Similarity	NPC285622
0.6524	Remote Similarity	NPC123241
0.6517	Remote Similarity	NPC243162
0.651	Remote Similarity	NPC469915
0.6505	Remote Similarity	NPC123395
0.65	Remote Similarity	NPC21638
0.6498	Remote Similarity	NPC52254
0.6488	Remote Similarity	NPC162440
0.648	Remote Similarity	NPC321211
0.6476	Remote Similarity	NPC277350
0.6476	Remote Similarity	NPC195787
0.6476	Remote Similarity	NPC246140
0.6473	Remote Similarity	NPC249150
0.6473	Remote Similarity	NPC195461
0.6473	Remote Similarity	NPC313985
0.6473	Remote Similarity	NPC214428
0.6473	Remote Similarity	NPC139373
0.6473	Remote Similarity	NPC79129
0.6473	Remote Similarity	NPC81654
0.6473	Remote Similarity	NPC49196
0.6471	Remote Similarity	NPC221687
0.6468	Remote Similarity	NPC63199
0.6468	Remote Similarity	NPC175474
0.6468	Remote Similarity	NPC196251
0.6468	Remote Similarity	NPC102338
0.6468	Remote Similarity	NPC111602
0.6455	Remote Similarity	NPC255229
0.6455	Remote Similarity	NPC81229
0.6453	Remote Similarity	NPC473004
0.6449	Remote Similarity	NPC472098
0.6432	Remote Similarity	NPC475763
0.6429	Remote Similarity	NPC14339
0.6429	Remote Similarity	NPC87714
0.6421	Remote Similarity	NPC476231
0.6419	Remote Similarity	NPC234078
0.6419	Remote Similarity	NPC221100
0.6396	Remote Similarity	NPC133261
0.6394	Remote Similarity	NPC138830
0.6393	Remote Similarity	NPC472099
0.6387	Remote Similarity	NPC313757
0.6386	Remote Similarity	NPC284706
0.6385	Remote Similarity	NPC469743
0.6383	Remote Similarity	NPC469536
0.6382	Remote Similarity	NPC139291
0.6382	Remote Similarity	NPC472108
0.6382	Remote Similarity	NPC472110
0.6382	Remote Similarity	NPC472109

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 NPC472209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	510
0.2-0.3	715
0.3-0.4	1768
0.4-0.5	4013
0.5-0.6	1842
0.6-0.7	126
0.7-0.8	3
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7586	Intermediate Similarity	NPD4120	Approved
0.7586	Intermediate Similarity	NPD4121	Phase 3
0.7543	Intermediate Similarity	NPD5742	Approved
0.7543	Intermediate Similarity	NPD5741	Approved
0.7543	Intermediate Similarity	NPD5743	Approved
0.6881	Remote Similarity	NPD4500	Approved
0.6881	Remote Similarity	NPD4501	Approved
0.6811	Remote Similarity	NPD7600	Phase 2
0.6716	Remote Similarity	NPD4602	Approved
0.6685	Remote Similarity	NPD4682	Phase 2
0.66	Remote Similarity	NPD4499	Approved
0.6585	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7599	Phase 2
0.6522	Remote Similarity	NPD7606	Phase 3
0.6514	Remote Similarity	NPD5184	Approved
0.6514	Remote Similarity	NPD5182	Approved
0.6514	Remote Similarity	NPD5185	Approved
0.6473	Remote Similarity	NPD4600	Approved
0.6473	Remote Similarity	NPD4601	Approved
0.6464	Remote Similarity	NPD7487	Discontinued
0.6462	Remote Similarity	NPD4506	Discontinued
0.6448	Remote Similarity	NPD7478	Approved
0.644	Remote Similarity	NPD7035	Approved
0.644	Remote Similarity	NPD7036	Phase 3
0.6422	Remote Similarity	NPD6770	Approved
0.6411	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7105	Phase 1
0.6382	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD4520	Approved
0.6305	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4041	Approved
0.63	Remote Similarity	NPD8281	Discontinued
0.6298	Remote Similarity	NPD7778	Approved
0.6298	Remote Similarity	NPD7777	Approved
0.6298	Remote Similarity	NPD53	Approved
0.6273	Remote Similarity	NPD7168	Phase 3
0.6256	Remote Similarity	NPD8325	Phase 3
0.6256	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7795	Phase 2
0.6256	Remote Similarity	NPD8326	Phase 3
0.6256	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD4427	Phase 2
0.6223	Remote Similarity	NPD3399	Approved
0.6219	Remote Similarity	NPD7962	Phase 2
0.621	Remote Similarity	NPD3389	Approved
0.621	Remote Similarity	NPD3393	Approved
0.621	Remote Similarity	NPD3394	Approved
0.6205	Remote Similarity	NPD2844	Phase 3
0.6198	Remote Similarity	NPD7244	Discontinued
0.6196	Remote Similarity	NPD2435	Approved
0.6181	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7869	Discontinued
0.6163	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7295	Approved
0.6162	Remote Similarity	NPD3423	Phase 2
0.6162	Remote Similarity	NPD3422	Phase 3
0.6143	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6635	Approved
0.6133	Remote Similarity	NPD2670	Approved
0.6126	Remote Similarity	NPD6570	Approved
0.6126	Remote Similarity	NPD6571	Approved
0.6114	Remote Similarity	NPD6874	Approved
0.6108	Remote Similarity	NPD3436	Approved
0.6103	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6642	Approved
0.61	Remote Similarity	NPD6641	Approved
0.608	Remote Similarity	NPD7940	Phase 3
0.6075	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7234	Approved
0.6068	Remote Similarity	NPD7233	Approved
0.6066	Remote Similarity	NPD4397	Phase 1
0.6064	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD7082	Approved
0.6048	Remote Similarity	NPD2607	Approved
0.604	Remote Similarity	NPD5897	Approved
0.604	Remote Similarity	NPD5899	Approved
0.604	Remote Similarity	NPD5898	Approved
0.603	Remote Similarity	NPD5997	Discontinued
0.6023	Remote Similarity	NPD2994	Approved
0.6022	Remote Similarity	NPD7259	Approved
0.6019	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7001	Phase 3
0.601	Remote Similarity	NPD3435	Discontinued
0.6009	Remote Similarity	NPD6529	Discontinued
0.6	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5982	Phase 2
0.6	Remote Similarity	NPD6227	Discontinued
0.599	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.599	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.599	Remote Similarity	NPD7775	Approved
0.5981	Remote Similarity	NPD7973	Discontinued
0.5981	Remote Similarity	NPD7570	Approved
0.5981	Remote Similarity	NPD7569	Approved
0.598	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5941	Approved
0.5979	Remote Similarity	NPD5942	Approved
0.5978	Remote Similarity	NPD4738	Phase 2
0.597	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD8007	Approved
0.5969	Remote Similarity	NPD2948	Discontinued
0.5969	Remote Similarity	NPD7882	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD8008	Approved
0.5968	Remote Similarity	NPD6301	Phase 2
0.5966	Remote Similarity	NPD5578	Approved
0.5966	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD2116	Approved
0.5965	Remote Similarity	NPD2117	Pre-registration
0.5965	Remote Similarity	NPD2115	Approved
0.5963	Remote Similarity	NPD7665	Phase 2
0.5963	Remote Similarity	NPD2510	Approved
0.5963	Remote Similarity	NPD2509	Approved
0.5963	Remote Similarity	NPD7666	Phase 3
0.5962	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6999	Discontinued
0.5959	Remote Similarity	NPD6913	Approved
0.5959	Remote Similarity	NPD1663	Discontinued
0.5957	Remote Similarity	NPD4607	Approved
0.5957	Remote Similarity	NPD6416	Phase 2
0.5955	Remote Similarity	NPD766	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7482	Phase 2
0.5951	Remote Similarity	NPD7483	Phase 2
0.595	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6182	Approved
0.595	Remote Similarity	NPD43	Approved
0.5941	Remote Similarity	NPD8358	Approved
0.5926	Remote Similarity	NPD1802	Approved
0.5926	Remote Similarity	NPD1801	Approved
0.5926	Remote Similarity	NPD3352	Approved
0.5926	Remote Similarity	NPD6176	Phase 1
0.5924	Remote Similarity	NPD3170	Approved
0.5922	Remote Similarity	NPD2613	Approved
0.5922	Remote Similarity	NPD5075	Discontinued
0.592	Remote Similarity	NPD2946	Phase 2
0.5914	Remote Similarity	NPD2923	Approved
0.5913	Remote Similarity	NPD6068	Discontinued
0.5911	Remote Similarity	NPD7881	Approved
0.5907	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD6185	Discontinued
0.5902	Remote Similarity	NPD2095	Phase 2
0.5902	Remote Similarity	NPD2094	Phase 2
0.5902	Remote Similarity	NPD2092	Phase 2
0.5896	Remote Similarity	NPD3030	Approved
0.5896	Remote Similarity	NPD2210	Approved
0.5896	Remote Similarity	NPD3032	Approved
0.5896	Remote Similarity	NPD6550	Discontinued
0.5896	Remote Similarity	NPD3031	Approved
0.5896	Remote Similarity	NPD2212	Approved
0.5895	Remote Similarity	NPD4432	Discontinued
0.5895	Remote Similarity	NPD7528	Approved
0.5891	Remote Similarity	NPD5104	Approved
0.5882	Remote Similarity	NPD6878	Phase 2
0.5882	Remote Similarity	NPD6879	Phase 2
0.5874	Remote Similarity	NPD7707	Approved
0.5874	Remote Similarity	NPD2096	Phase 2
0.5874	Remote Similarity	NPD2091	Phase 2
0.5872	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD3377	Discontinued
0.587	Remote Similarity	NPD2567	Approved
0.587	Remote Similarity	NPD2569	Approved
0.587	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.5869	Remote Similarity	NPD5003	Discontinued
0.5865	Remote Similarity	NPD8020	Approved
0.5865	Remote Similarity	NPD8021	Approved
0.5864	Remote Similarity	NPD4513	Discontinued
0.5864	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5430	Discontinued
0.5857	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD5042	Phase 1
0.5853	Remote Similarity	NPD7205	Discontinued
0.5851	Remote Similarity	NPD2387	Approved
0.5848	Remote Similarity	NPD8160	Phase 2
0.5847	Remote Similarity	NPD1071	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5466	Approved
0.5842	Remote Similarity	NPD6758	Approved
0.5837	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.5837	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4365	Phase 2
0.583	Remote Similarity	NPD7708	Approved
0.5826	Remote Similarity	NPD5426	Phase 3
0.5826	Remote Similarity	NPD6987	Phase 1
0.5826	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5596	Phase 2
0.5824	Remote Similarity	NPD3090	Approved
0.5824	Remote Similarity	NPD3614	Approved
0.5824	Remote Similarity	NPD3088	Approved
0.5824	Remote Similarity	NPD2573	Approved
0.5824	Remote Similarity	NPD3089	Approved
0.5824	Remote Similarity	NPD2566	Approved
0.5824	Remote Similarity	NPD2574	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