NPASS Compound

Structure

NPC121036 OpenBabel07101718232D 37 39 0 0 1 0 0 0 0 0999 V2000 3.0640 -5.0653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4638 -5.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9252 -4.3152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2101 -4.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3365 3.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7203 2.5174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2140 1.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8613 0.8815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6253 -1.5206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6899 -4.0109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2987 -3.2175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8582 -2.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1262 1.8398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0692 -2.5767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5174 0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5741 -1.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9160 -2.2936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1619 -1.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0726 -4.9347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9978 -3.9411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7276 2.6388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8832 0.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1619 -1.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9160 -2.2936 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5741 -0.2775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6231 -0.5865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9160 0.1206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2089 -0.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3536 -0.8536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6231 -1.5865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2089 -1.5865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9160 0.1206 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6619 -0.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2987 1.0445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7150 -0.2038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3450 -0.9841 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 22 1 0 0 0 0 10 11 1 0 0 0 0 10 19 2 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 13 15 1 0 0 0 0 13 21 2 0 0 0 0 16 23 1 0 0 0 0 16 30 1 0 0 0 0 17 24 1 0 0 0 0 17 31 1 0 0 0 0 18 23 1 0 0 0 0 18 33 2 0 0 0 0 22 25 1 0 0 0 0 23 25 2 0 0 0 0 24 30 1 1 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 26 30 1 1 0 0 0 27 32 1 0 0 0 0 27 34 2 0 0 0 0 28 31 1 0 0 0 0 28 32 1 0 0 0 0 28 35 2 0 0 0 0 29 31 1 0 0 0 0 29 36 2 0 0 0 0 29 37 1 0 0 0 0 30 9 1 1 0 0 0 31 14 1 6 0 0 0 32 15 1 6 0 0 0 32 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.32
Volume:	559.218
LogP:	6.807
LogD:	4.937
LogS:	-5.21
# Rotatable Bonds:	8
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.158
Synthetic Accessibility Score:	6.064
Fsp3:	0.625
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	1.8663260561879724e-05
Pgp-inhibitor:	0.263
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.954
Plasma Protein Binding (PPB):	77.99561309814453%
Volume Distribution (VD):	3.2
Pgp-substrate:	8.638736724853516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.31
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.881
CYP3A4-substrate:	0.89

ADMET: Excretion

Clearance (CL):	13.774
Half-life (T1/2):	0.009

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.905
AMES Toxicity:	0.407
Rat Oral Acute Toxicity:	0.273
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.848
Carcinogencity:	0.862
Eye Corrosion:	0.027
Eye Irritation:	0.05
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC121036

Natural Product ID:	NPC121036
*Common Name:**	AEVDRGYEHJFKLT-UXSGCWECSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AEVDRGYEHJFKLT-UXSGCWECSA-N
Standard InCHI:	InChI=1S/C32H44O5/c1-19(2)10-11-24-17-31(14-12-20(3)4)28(35)32(37-29(31)36,15-13-21(5)6)27(34)26-25(22(7)8)23(18-33)16-30(24,26)9/h10,12-13,18,22,24,26H,11,14-17H2,1-9H3/t24-,26+,30+,31+,32-/m0/s1
SMILES:	CC(=CC[C@H]1C[C@]2(CC=C(C)C)C(=O)[C@](CC=C(C)C)(C(=O)[C@H]3C(=C(C[C@]13C)C=O)C(C)C)OC2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581582
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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	5
Others	1

Activity Type	# Activity
Cell Line	5
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	-100.0	%	PMID[501649]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[501649]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[501649]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[501649]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[501649]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[501649]

☑ 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 NPC121036 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	252
0.1-0.2	1951
0.2-0.3	8461
0.3-0.4	15126
0.4-0.5	8825
0.5-0.6	6346
0.6-0.7	1650
0.7-0.8	77
0.8-0.85	5
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472674
0.8876	High Similarity	NPC472686
0.8876	High Similarity	NPC290329
0.7822	Intermediate Similarity	NPC54843
0.77	Intermediate Similarity	NPC31021
0.77	Intermediate Similarity	NPC474490
0.7624	Intermediate Similarity	NPC476275
0.7604	Intermediate Similarity	NPC279859
0.7604	Intermediate Similarity	NPC38576
0.7526	Intermediate Similarity	NPC471739
0.75	Intermediate Similarity	NPC202824
0.75	Intermediate Similarity	NPC477361
0.7451	Intermediate Similarity	NPC477354
0.7447	Intermediate Similarity	NPC39411
0.7447	Intermediate Similarity	NPC286229
0.7447	Intermediate Similarity	NPC255580
0.7429	Intermediate Similarity	NPC25639
0.7423	Intermediate Similarity	NPC70555
0.7423	Intermediate Similarity	NPC70422
0.7423	Intermediate Similarity	NPC104961
0.7419	Intermediate Similarity	NPC276647
0.7419	Intermediate Similarity	NPC622
0.7419	Intermediate Similarity	NPC471740
0.74	Intermediate Similarity	NPC74103
0.74	Intermediate Similarity	NPC150978
0.74	Intermediate Similarity	NPC70595
0.74	Intermediate Similarity	NPC123177
0.7396	Intermediate Similarity	NPC475796
0.7391	Intermediate Similarity	NPC195785
0.7391	Intermediate Similarity	NPC15975
0.7391	Intermediate Similarity	NPC266124
0.732	Intermediate Similarity	NPC33570
0.732	Intermediate Similarity	NPC21471
0.73	Intermediate Similarity	NPC471818
0.73	Intermediate Similarity	NPC253144
0.73	Intermediate Similarity	NPC2946
0.7292	Intermediate Similarity	NPC215294
0.7292	Intermediate Similarity	NPC108045
0.7292	Intermediate Similarity	NPC475622
0.729	Intermediate Similarity	NPC472756
0.729	Intermediate Similarity	NPC13385
0.7273	Intermediate Similarity	NPC471047
0.7273	Intermediate Similarity	NPC190718
0.7273	Intermediate Similarity	NPC475906
0.7273	Intermediate Similarity	NPC469628
0.7273	Intermediate Similarity	NPC469653
0.7273	Intermediate Similarity	NPC469631
0.7255	Intermediate Similarity	NPC148463
0.7234	Intermediate Similarity	NPC28319
0.7228	Intermediate Similarity	NPC284185
0.7216	Intermediate Similarity	NPC238197
0.7212	Intermediate Similarity	NPC87090
0.72	Intermediate Similarity	NPC41217
0.7196	Intermediate Similarity	NPC271059
0.7196	Intermediate Similarity	NPC25666
0.7188	Intermediate Similarity	NPC173609
0.7174	Intermediate Similarity	NPC469669
0.7174	Intermediate Similarity	NPC475771
0.7174	Intermediate Similarity	NPC469678
0.7172	Intermediate Similarity	NPC38885
0.717	Intermediate Similarity	NPC472685
0.717	Intermediate Similarity	NPC472702
0.717	Intermediate Similarity	NPC477356
0.717	Intermediate Similarity	NPC195192
0.717	Intermediate Similarity	NPC304738
0.7158	Intermediate Similarity	NPC304795
0.7158	Intermediate Similarity	NPC223904
0.7143	Intermediate Similarity	NPC275439
0.7143	Intermediate Similarity	NPC477355
0.7143	Intermediate Similarity	NPC161957
0.7143	Intermediate Similarity	NPC470188
0.7143	Intermediate Similarity	NPC78089
0.7143	Intermediate Similarity	NPC112753
0.7129	Intermediate Similarity	NPC306168
0.7129	Intermediate Similarity	NPC477711
0.7129	Intermediate Similarity	NPC49946
0.7129	Intermediate Similarity	NPC329857
0.7129	Intermediate Similarity	NPC469718
0.7115	Intermediate Similarity	NPC318082
0.7103	Intermediate Similarity	NPC118405
0.7103	Intermediate Similarity	NPC105725
0.7087	Intermediate Similarity	NPC56525
0.7087	Intermediate Similarity	NPC167219
0.708	Intermediate Similarity	NPC472929
0.7075	Intermediate Similarity	NPC474802
0.7071	Intermediate Similarity	NPC107787
0.7064	Intermediate Similarity	NPC470267
0.7064	Intermediate Similarity	NPC314244
0.7064	Intermediate Similarity	NPC291643
0.7059	Intermediate Similarity	NPC111114
0.7059	Intermediate Similarity	NPC300312
0.7059	Intermediate Similarity	NPC20713
0.7059	Intermediate Similarity	NPC261607
0.7053	Intermediate Similarity	NPC469620
0.7053	Intermediate Similarity	NPC469690
0.7048	Intermediate Similarity	NPC292133
0.7048	Intermediate Similarity	NPC169205
0.7048	Intermediate Similarity	NPC216904
0.7041	Intermediate Similarity	NPC165287
0.7041	Intermediate Similarity	NPC100391
0.7041	Intermediate Similarity	NPC115786
0.7041	Intermediate Similarity	NPC470918
0.7037	Intermediate Similarity	NPC474207
0.7037	Intermediate Similarity	NPC474330
0.703	Intermediate Similarity	NPC52198
0.703	Intermediate Similarity	NPC117405
0.703	Intermediate Similarity	NPC305039
0.703	Intermediate Similarity	NPC473039
0.7021	Intermediate Similarity	NPC122264
0.7019	Intermediate Similarity	NPC48803
0.7019	Intermediate Similarity	NPC275960
0.7019	Intermediate Similarity	NPC193645
0.7019	Intermediate Similarity	NPC90121
0.701	Intermediate Similarity	NPC256750
0.701	Intermediate Similarity	NPC20262
0.7009	Intermediate Similarity	NPC472753
0.7009	Intermediate Similarity	NPC270155
0.7009	Intermediate Similarity	NPC475867
0.7	Intermediate Similarity	NPC197333
0.7	Intermediate Similarity	NPC237540
0.6991	Remote Similarity	NPC477093
0.6991	Remote Similarity	NPC475277
0.6991	Remote Similarity	NPC473522
0.699	Remote Similarity	NPC476597
0.699	Remote Similarity	NPC474185
0.699	Remote Similarity	NPC165383
0.699	Remote Similarity	NPC475302
0.699	Remote Similarity	NPC476598
0.6981	Remote Similarity	NPC141191
0.6979	Remote Similarity	NPC276356
0.6979	Remote Similarity	NPC302426
0.6979	Remote Similarity	NPC69271
0.6979	Remote Similarity	NPC74673
0.697	Remote Similarity	NPC125290
0.697	Remote Similarity	NPC470223
0.6957	Remote Similarity	NPC470237
0.6952	Remote Similarity	NPC269492
0.6952	Remote Similarity	NPC184065
0.6952	Remote Similarity	NPC185553
0.6947	Remote Similarity	NPC474056
0.6944	Remote Similarity	NPC49393
0.6944	Remote Similarity	NPC53222
0.6944	Remote Similarity	NPC78127
0.6944	Remote Similarity	NPC471757
0.6944	Remote Similarity	NPC271266
0.6944	Remote Similarity	NPC308351
0.6944	Remote Similarity	NPC472754
0.6939	Remote Similarity	NPC39588
0.6939	Remote Similarity	NPC8091
0.6931	Remote Similarity	NPC477710
0.6931	Remote Similarity	NPC475902
0.6923	Remote Similarity	NPC469819
0.6923	Remote Similarity	NPC94425
0.6923	Remote Similarity	NPC289004
0.6923	Remote Similarity	NPC114162
0.6923	Remote Similarity	NPC476596
0.6923	Remote Similarity	NPC472933
0.6923	Remote Similarity	NPC469632
0.6916	Remote Similarity	NPC470906
0.6916	Remote Similarity	NPC472728
0.6916	Remote Similarity	NPC472727
0.6915	Remote Similarity	NPC472959
0.6915	Remote Similarity	NPC471726
0.6915	Remote Similarity	NPC474527
0.6915	Remote Similarity	NPC226242
0.6907	Remote Similarity	NPC10276
0.6907	Remote Similarity	NPC35089
0.6903	Remote Similarity	NPC43775
0.6903	Remote Similarity	NPC475495
0.69	Remote Similarity	NPC474045
0.69	Remote Similarity	NPC238593
0.69	Remote Similarity	NPC261253
0.69	Remote Similarity	NPC469676
0.6897	Remote Similarity	NPC472934
0.6897	Remote Similarity	NPC472927
0.6893	Remote Similarity	NPC221282
0.6887	Remote Similarity	NPC213947
0.6887	Remote Similarity	NPC170143
0.6887	Remote Similarity	NPC23680
0.6887	Remote Similarity	NPC108475
0.6882	Remote Similarity	NPC469643
0.6882	Remote Similarity	NPC469641
0.6882	Remote Similarity	NPC167049
0.6882	Remote Similarity	NPC469691
0.6881	Remote Similarity	NPC36321
0.6881	Remote Similarity	NPC475873
0.6881	Remote Similarity	NPC472755
0.6875	Remote Similarity	NPC23497
0.6869	Remote Similarity	NPC320801
0.6869	Remote Similarity	NPC475100
0.6869	Remote Similarity	NPC149869
0.6869	Remote Similarity	NPC474359
0.6869	Remote Similarity	NPC32565
0.6869	Remote Similarity	NPC120726
0.6864	Remote Similarity	NPC147635
0.6864	Remote Similarity	NPC163693
0.6863	Remote Similarity	NPC469546
0.6863	Remote Similarity	NPC474570
0.6863	Remote Similarity	NPC476388
0.6863	Remote Similarity	NPC477215

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 NPC121036 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	2604
0.2-0.3	4034
0.3-0.4	1590
0.4-0.5	407
0.5-0.6	219
0.6-0.7	62
0.7-0.8	0
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
0.7273	Intermediate Similarity	NPD6672	Approved
0.7273	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD5696	Approved
0.7087	Intermediate Similarity	NPD5282	Discontinued
0.703	Intermediate Similarity	NPD6673	Approved
0.703	Intermediate Similarity	NPD6904	Approved
0.703	Intermediate Similarity	NPD6080	Approved
0.7019	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6050	Approved
0.6887	Remote Similarity	NPD6083	Phase 2
0.6887	Remote Similarity	NPD6084	Phase 2
0.6857	Remote Similarity	NPD5695	Phase 3
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5692	Phase 3
0.6735	Remote Similarity	NPD5369	Approved
0.6733	Remote Similarity	NPD6098	Approved
0.6731	Remote Similarity	NPD5694	Approved
0.6731	Remote Similarity	NPD5693	Phase 1
0.6637	Remote Similarity	NPD7320	Approved
0.6635	Remote Similarity	NPD5785	Approved
0.6635	Remote Similarity	NPD5207	Approved
0.6607	Remote Similarity	NPD5739	Approved
0.6607	Remote Similarity	NPD6008	Approved
0.6607	Remote Similarity	NPD6402	Approved
0.6607	Remote Similarity	NPD6675	Approved
0.6607	Remote Similarity	NPD7128	Approved
0.6602	Remote Similarity	NPD6903	Approved
0.6579	Remote Similarity	NPD6372	Approved
0.6579	Remote Similarity	NPD6373	Approved
0.6569	Remote Similarity	NPD7146	Approved
0.6569	Remote Similarity	NPD6684	Approved
0.6569	Remote Similarity	NPD6409	Approved
0.6569	Remote Similarity	NPD5330	Approved
0.6569	Remote Similarity	NPD7521	Approved
0.6569	Remote Similarity	NPD7334	Approved
0.6549	Remote Similarity	NPD6614	Approved
0.6538	Remote Similarity	NPD1695	Approved
0.6509	Remote Similarity	NPD6399	Phase 3
0.65	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6899	Approved
0.6491	Remote Similarity	NPD6881	Approved
0.6471	Remote Similarity	NPD5363	Approved
0.6466	Remote Similarity	NPD8130	Phase 1
0.6466	Remote Similarity	NPD6650	Approved
0.6466	Remote Similarity	NPD6649	Approved
0.6449	Remote Similarity	NPD6001	Approved
0.6442	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5362	Discontinued
0.641	Remote Similarity	NPD8297	Approved
0.6408	Remote Similarity	NPD5786	Approved
0.6404	Remote Similarity	NPD5697	Approved
0.6404	Remote Similarity	NPD5701	Approved
0.6389	Remote Similarity	NPD5654	Approved
0.6389	Remote Similarity	NPD4629	Approved
0.6389	Remote Similarity	NPD5210	Approved
0.6379	Remote Similarity	NPD7102	Approved
0.6379	Remote Similarity	NPD6371	Approved
0.6379	Remote Similarity	NPD7290	Approved
0.6379	Remote Similarity	NPD6883	Approved
0.6348	Remote Similarity	NPD6011	Approved
0.6337	Remote Similarity	NPD4270	Approved
0.6337	Remote Similarity	NPD4269	Approved
0.6337	Remote Similarity	NPD5209	Approved
0.6337	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4697	Phase 3
0.6325	Remote Similarity	NPD6869	Approved
0.6325	Remote Similarity	NPD6617	Approved
0.6325	Remote Similarity	NPD6847	Approved
0.6325	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1694	Approved
0.6296	Remote Similarity	NPD7900	Approved
0.6296	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6014	Approved
0.6293	Remote Similarity	NPD6013	Approved
0.6293	Remote Similarity	NPD6012	Approved
0.6286	Remote Similarity	NPD5208	Approved
0.6283	Remote Similarity	NPD6052	Approved
0.6273	Remote Similarity	NPD5959	Approved
0.6271	Remote Similarity	NPD6882	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6263	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6411	Approved
0.624	Remote Similarity	NPD7492	Approved
0.6226	Remote Similarity	NPD4753	Phase 2
0.622	Remote Similarity	NPD7736	Approved
0.619	Remote Similarity	NPD6616	Approved
0.6179	Remote Similarity	NPD6059	Approved
0.6179	Remote Similarity	NPD6054	Approved
0.6176	Remote Similarity	NPD6435	Approved
0.6154	Remote Similarity	NPD5329	Approved
0.6147	Remote Similarity	NPD7748	Approved
0.6142	Remote Similarity	NPD7078	Approved
0.6139	Remote Similarity	NPD4252	Approved
0.6126	Remote Similarity	NPD7902	Approved
0.6117	Remote Similarity	NPD7154	Phase 3
0.6111	Remote Similarity	NPD5284	Approved
0.6111	Remote Similarity	NPD5281	Approved
0.6095	Remote Similarity	NPD5279	Phase 3
0.608	Remote Similarity	NPD6370	Approved
0.6075	Remote Similarity	NPD6101	Approved
0.6075	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7115	Discovery
0.6058	Remote Similarity	NPD4197	Approved
0.6048	Remote Similarity	NPD6319	Approved
0.6038	Remote Similarity	NPD3573	Approved
0.6036	Remote Similarity	NPD7732	Phase 3
0.6016	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6868	Approved
0.5984	Remote Similarity	NPD6274	Approved
0.5982	Remote Similarity	NPD4755	Approved
0.598	Remote Similarity	NPD5368	Approved
0.598	Remote Similarity	NPD4695	Discontinued
0.5968	Remote Similarity	NPD7100	Approved
0.5968	Remote Similarity	NPD7101	Approved
0.596	Remote Similarity	NPD8039	Approved
0.5952	Remote Similarity	NPD5988	Approved
0.5943	Remote Similarity	NPD5690	Phase 2
0.5943	Remote Similarity	NPD4694	Approved
0.5943	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5280	Approved
0.5935	Remote Similarity	NPD6317	Approved
0.5929	Remote Similarity	NPD4225	Approved
0.5926	Remote Similarity	NPD5328	Approved
0.5926	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5778	Approved
0.5909	Remote Similarity	NPD5779	Approved
0.5905	Remote Similarity	NPD4786	Approved
0.5893	Remote Similarity	NPD5222	Approved
0.5893	Remote Similarity	NPD5221	Approved
0.5893	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6314	Approved
0.5887	Remote Similarity	NPD6313	Approved
0.5877	Remote Similarity	NPD4700	Approved
0.5877	Remote Similarity	NPD5286	Approved
0.5877	Remote Similarity	NPD4696	Approved
0.5877	Remote Similarity	NPD5285	Approved
0.5873	Remote Similarity	NPD6908	Approved
0.5873	Remote Similarity	NPD6909	Approved
0.5865	Remote Similarity	NPD4223	Phase 3
0.5865	Remote Similarity	NPD4221	Approved
0.5849	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6033	Approved
0.5841	Remote Similarity	NPD5173	Approved
0.5826	Remote Similarity	NPD5223	Approved
0.582	Remote Similarity	NPD4632	Approved
0.5818	Remote Similarity	NPD6079	Approved
0.5818	Remote Similarity	NPD7515	Phase 2
0.5818	Remote Similarity	NPD8034	Phase 2
0.5818	Remote Similarity	NPD8035	Phase 2
0.5818	Remote Similarity	NPD7637	Suspended
0.5818	Remote Similarity	NPD7983	Approved
0.581	Remote Similarity	NPD5331	Approved
0.581	Remote Similarity	NPD5332	Approved
0.5806	Remote Similarity	NPD6009	Approved
0.5794	Remote Similarity	NPD3618	Phase 1
0.5789	Remote Similarity	NPD7331	Phase 2
0.5789	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD7604	Phase 2
0.5781	Remote Similarity	NPD8328	Phase 3
0.5776	Remote Similarity	NPD5224	Approved
0.5776	Remote Similarity	NPD5225	Approved
0.5776	Remote Similarity	NPD5211	Phase 2
0.5776	Remote Similarity	NPD5091	Approved
0.5776	Remote Similarity	NPD5226	Approved
0.5776	Remote Similarity	NPD4633	Approved
0.5769	Remote Similarity	NPD4790	Discontinued
0.5755	Remote Similarity	NPD3665	Phase 1
0.5755	Remote Similarity	NPD3666	Approved
0.5755	Remote Similarity	NPD3133	Approved
0.5755	Remote Similarity	NPD3668	Phase 3
0.5748	Remote Similarity	NPD5983	Phase 2
0.5738	Remote Similarity	NPD6053	Discontinued
0.5726	Remote Similarity	NPD4754	Approved
0.5726	Remote Similarity	NPD5174	Approved
0.5726	Remote Similarity	NPD5175	Approved
0.5725	Remote Similarity	NPD8337	Approved
0.5725	Remote Similarity	NPD8336	Approved
0.5714	Remote Similarity	NPD3667	Approved
0.5702	Remote Similarity	NPD4634	Approved
0.5692	Remote Similarity	NPD6336	Discontinued
0.5688	Remote Similarity	NPD4518	Approved
0.5686	Remote Similarity	NPD4756	Discovery
0.5684	Remote Similarity	NPD7341	Phase 2
0.5682	Remote Similarity	NPD7319	Approved
0.5678	Remote Similarity	NPD5141	Approved
0.5673	Remote Similarity	NPD4822	Approved
0.5673	Remote Similarity	NPD4821	Approved
0.5673	Remote Similarity	NPD4820	Approved
0.5673	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4819	Approved
0.5673	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7122	Discontinued
0.5652	Remote Similarity	NPD7638	Approved
0.5648	Remote Similarity	NPD4690	Approved
0.5648	Remote Similarity	NPD4688	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