NPASS Compound

Structure

NPC474378 OpenBabel07101719512D 31 34 0 0 1 0 0 0 0 0999 V2000 -1.8733 -2.3913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5038 -2.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6033 -0.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0230 2.3576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8686 -0.5512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7455 0.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8087 -0.7931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8087 1.6498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9093 -0.3263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5811 -1.7345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2505 -1.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3663 -0.7931 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7455 0.1565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2163 -0.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2163 0.9719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3063 1.4079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3063 -0.5512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8686 1.4079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5792 0.7726 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9203 -0.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3663 1.6498 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9587 -0.1153 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9093 -1.2918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8525 -1.9171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4706 2.1628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1909 -1.4830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0817 2.5725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7043 -1.3061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3403 0.4283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1352 0.9126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 5 12 1 0 0 0 0 5 14 1 0 0 0 0 6 13 1 0 0 0 0 6 15 2 0 0 0 0 7 12 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 13 1 0 0 0 0 9 23 2 0 0 0 0 11 24 2 0 0 0 0 11 28 1 0 0 0 0 12 10 1 1 0 0 0 13 14 2 0 0 0 0 14 29 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 8 1 1 0 0 0 16 19 1 0 0 0 0 16 30 1 0 0 0 0 17 22 1 6 0 0 0 17 28 1 0 0 0 0 18 21 1 6 0 0 0 18 25 1 0 0 0 0 19 22 1 1 0 0 0 19 31 1 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 4 1 1 0 0 0 21 27 1 0 0 0 0 22 20 1 6 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.16
Volume:	418.136
LogP:	2.241
LogD:	1.112
LogS:	-4.146
# Rotatable Bonds:	4
TPSA:	135.8
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	6.586
Fsp3:	0.591
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:	-5.404
MDCK Permeability:	4.8995367251336575e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.264
Human Intestinal Absorption (HIA):	0.756
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	69.54663848876953%
Volume Distribution (VD):	1.374
Pgp-substrate:	27.0992431640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.294
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	3.495
Half-life (T1/2):	0.365

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.916
Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.494
Carcinogencity:	0.843
Eye Corrosion:	0.009
Eye Irritation:	0.03
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC474378

Natural Product ID:	NPC474378
*Common Name:**	Lophodiol B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HDOFLMSTYCZGEX-QSJUJLHKSA-N
Standard InCHI:	InChI=1S/C22H26O9/c1-10(2)12-5-14-13(9-23)6-15(29-14)18(25)21(4,27)8-16-19-22(31-19,20(26)30-16)17(7-12)28-11(3)24/h6,9,12,16-19,25,27H,1,5,7-8H2,2-4H3/t12-,16-,17+,18-,19-,21+,22-/m0/s1
SMILES:	O=Cc1cc2oc1C[C@@H](C[C@@H](OC(=O)C)[C@@]13[C@H]([C@H](C[C@@]([C@H]2O)(C)O)OC3=O)O1)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465762
PubChem CID:	16099470
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32683	lophogorgia peruana	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190454]

☑ 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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	14700.0	nM	PMID[463756]

☑ 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 NPC474378 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	341
0.1-0.2	1325
0.2-0.3	3847
0.3-0.4	8236
0.4-0.5	10548
0.5-0.6	7438
0.6-0.7	8709
0.7-0.8	2183
0.8-0.85	42
0.85-0.9	10
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474219
0.9583	High Similarity	NPC475864
0.9452	High Similarity	NPC474255
0.9452	High Similarity	NPC471618
0.9452	High Similarity	NPC474220
0.9388	High Similarity	NPC474270
0.9388	High Similarity	NPC475904
0.9379	High Similarity	NPC195920
0.9252	High Similarity	NPC474317
0.9247	High Similarity	NPC37488
0.911	High Similarity	NPC254198
0.9054	High Similarity	NPC104924
0.898	High Similarity	NPC110305
0.8966	High Similarity	NPC107571
0.8904	High Similarity	NPC282973
0.8759	High Similarity	NPC303217
0.8716	High Similarity	NPC248795
0.8707	High Similarity	NPC474615
0.8571	High Similarity	NPC473268
0.8562	High Similarity	NPC159786
0.8493	Intermediate Similarity	NPC106247
0.8421	Intermediate Similarity	NPC218712
0.8421	Intermediate Similarity	NPC267004
0.8421	Intermediate Similarity	NPC307346
0.8421	Intermediate Similarity	NPC261733
0.8367	Intermediate Similarity	NPC200718
0.8356	Intermediate Similarity	NPC97740
0.8356	Intermediate Similarity	NPC45358
0.8355	Intermediate Similarity	NPC22248
0.8333	Intermediate Similarity	NPC261184
0.8322	Intermediate Similarity	NPC286130
0.8299	Intermediate Similarity	NPC474407
0.8299	Intermediate Similarity	NPC474426
0.8299	Intermediate Similarity	NPC474425
0.8288	Intermediate Similarity	NPC17681
0.8288	Intermediate Similarity	NPC136340
0.8231	Intermediate Similarity	NPC471544
0.8231	Intermediate Similarity	NPC471545
0.8231	Intermediate Similarity	NPC473344
0.8228	Intermediate Similarity	NPC470380
0.8221	Intermediate Similarity	NPC123088
0.8214	Intermediate Similarity	NPC472665
0.8187	Intermediate Similarity	NPC474542
0.8182	Intermediate Similarity	NPC137295
0.8176	Intermediate Similarity	NPC114880
0.8171	Intermediate Similarity	NPC121995
0.816	Intermediate Similarity	NPC283209
0.816	Intermediate Similarity	NPC285567
0.8129	Intermediate Similarity	NPC10302
0.8129	Intermediate Similarity	NPC105381
0.8121	Intermediate Similarity	NPC476850
0.8121	Intermediate Similarity	NPC476861
0.8121	Intermediate Similarity	NPC472651
0.8098	Intermediate Similarity	NPC193798
0.8095	Intermediate Similarity	NPC45947
0.8086	Intermediate Similarity	NPC472779
0.8086	Intermediate Similarity	NPC116639
0.8075	Intermediate Similarity	NPC469485
0.8072	Intermediate Similarity	NPC472652
0.8072	Intermediate Similarity	NPC271235
0.8061	Intermediate Similarity	NPC475779
0.8049	Intermediate Similarity	NPC14822
0.8049	Intermediate Similarity	NPC288602
0.8049	Intermediate Similarity	NPC88841
0.8037	Intermediate Similarity	NPC477402
0.8037	Intermediate Similarity	NPC287559
0.8037	Intermediate Similarity	NPC25255
0.8025	Intermediate Similarity	NPC304692
0.8025	Intermediate Similarity	NPC261597
0.8025	Intermediate Similarity	NPC36655
0.8025	Intermediate Similarity	NPC187149
0.8025	Intermediate Similarity	NPC173544
0.8014	Intermediate Similarity	NPC471501
0.8014	Intermediate Similarity	NPC137570
0.8014	Intermediate Similarity	NPC474830
0.8014	Intermediate Similarity	NPC471554
0.8014	Intermediate Similarity	NPC473355
0.8014	Intermediate Similarity	NPC471573
0.8012	Intermediate Similarity	NPC473766
0.8012	Intermediate Similarity	NPC75310
0.8012	Intermediate Similarity	NPC473753
0.8012	Intermediate Similarity	NPC270312
0.8012	Intermediate Similarity	NPC214541
0.8012	Intermediate Similarity	NPC301233
0.8012	Intermediate Similarity	NPC44675
0.8	Intermediate Similarity	NPC476856
0.8	Intermediate Similarity	NPC75906
0.8	Intermediate Similarity	NPC56358
0.8	Intermediate Similarity	NPC474829
0.8	Intermediate Similarity	NPC44577
0.8	Intermediate Similarity	NPC476858
0.8	Intermediate Similarity	NPC476857
0.7988	Intermediate Similarity	NPC303210
0.7988	Intermediate Similarity	NPC239270
0.7988	Intermediate Similarity	NPC68848
0.7988	Intermediate Similarity	NPC49009
0.7988	Intermediate Similarity	NPC472584
0.7988	Intermediate Similarity	NPC117986
0.7988	Intermediate Similarity	NPC18986
0.7988	Intermediate Similarity	NPC169
0.7988	Intermediate Similarity	NPC95472
0.7988	Intermediate Similarity	NPC188649
0.7988	Intermediate Similarity	NPC5079
0.7976	Intermediate Similarity	NPC159232
0.7976	Intermediate Similarity	NPC294512
0.7975	Intermediate Similarity	NPC477403
0.7975	Intermediate Similarity	NPC473368
0.7975	Intermediate Similarity	NPC140952
0.7975	Intermediate Similarity	NPC475967
0.7963	Intermediate Similarity	NPC104736
0.7961	Intermediate Similarity	NPC186626
0.7959	Intermediate Similarity	NPC474438
0.7959	Intermediate Similarity	NPC474279
0.7952	Intermediate Similarity	NPC23387
0.7949	Intermediate Similarity	NPC476310
0.7949	Intermediate Similarity	NPC86935
0.7949	Intermediate Similarity	NPC476164
0.7939	Intermediate Similarity	NPC234660
0.7939	Intermediate Similarity	NPC51568
0.7939	Intermediate Similarity	NPC134254
0.7939	Intermediate Similarity	NPC302369
0.7939	Intermediate Similarity	NPC39986
0.7935	Intermediate Similarity	NPC473152
0.7929	Intermediate Similarity	NPC120220
0.7927	Intermediate Similarity	NPC335761
0.7927	Intermediate Similarity	NPC305016
0.7927	Intermediate Similarity	NPC472653
0.7927	Intermediate Similarity	NPC333139
0.7925	Intermediate Similarity	NPC211625
0.7917	Intermediate Similarity	NPC476459
0.7917	Intermediate Similarity	NPC470995
0.7914	Intermediate Similarity	NPC194499
0.7914	Intermediate Similarity	NPC81405
0.7914	Intermediate Similarity	NPC299038
0.7914	Intermediate Similarity	NPC45101
0.7914	Intermediate Similarity	NPC88007
0.7914	Intermediate Similarity	NPC472778
0.7914	Intermediate Similarity	NPC472776
0.7914	Intermediate Similarity	NPC472777
0.7911	Intermediate Similarity	NPC250228
0.7904	Intermediate Similarity	NPC476853
0.7904	Intermediate Similarity	NPC472282
0.7892	Intermediate Similarity	NPC476860
0.7892	Intermediate Similarity	NPC472664
0.7892	Intermediate Similarity	NPC271657
0.7891	Intermediate Similarity	NPC476016
0.7888	Intermediate Similarity	NPC475777
0.7888	Intermediate Similarity	NPC471613
0.7888	Intermediate Similarity	NPC268905
0.7879	Intermediate Similarity	NPC329938
0.7879	Intermediate Similarity	NPC263432
0.7866	Intermediate Similarity	NPC84349
0.7866	Intermediate Similarity	NPC269495
0.7862	Intermediate Similarity	NPC19747
0.7862	Intermediate Similarity	NPC7388
0.7857	Intermediate Similarity	NPC471397
0.7857	Intermediate Similarity	NPC472895
0.7857	Intermediate Similarity	NPC296558
0.7857	Intermediate Similarity	NPC323137
0.7853	Intermediate Similarity	NPC41880
0.7853	Intermediate Similarity	NPC99381
0.7849	Intermediate Similarity	NPC107244
0.7844	Intermediate Similarity	NPC86800
0.7843	Intermediate Similarity	NPC170604
0.7843	Intermediate Similarity	NPC215109
0.784	Intermediate Similarity	NPC57998
0.784	Intermediate Similarity	NPC275878
0.7836	Intermediate Similarity	NPC56953
0.7836	Intermediate Similarity	NPC176413
0.7831	Intermediate Similarity	NPC477405
0.7829	Intermediate Similarity	NPC14650
0.7826	Intermediate Similarity	NPC18135
0.7826	Intermediate Similarity	NPC475717
0.7824	Intermediate Similarity	NPC51404
0.7823	Intermediate Similarity	NPC329694
0.7823	Intermediate Similarity	NPC81912
0.7823	Intermediate Similarity	NPC329922
0.7823	Intermediate Similarity	NPC474260
0.7818	Intermediate Similarity	NPC470789
0.7818	Intermediate Similarity	NPC191828
0.7811	Intermediate Similarity	NPC472659
0.7811	Intermediate Similarity	NPC186392
0.7811	Intermediate Similarity	NPC302392
0.7808	Intermediate Similarity	NPC118853
0.7805	Intermediate Similarity	NPC470118
0.7805	Intermediate Similarity	NPC286722
0.7805	Intermediate Similarity	NPC195954
0.7799	Intermediate Similarity	NPC221809
0.7798	Intermediate Similarity	NPC204088
0.7798	Intermediate Similarity	NPC259007
0.7798	Intermediate Similarity	NPC173516
0.7798	Intermediate Similarity	NPC329215
0.7791	Intermediate Similarity	NPC53917
0.7791	Intermediate Similarity	NPC224165
0.7791	Intermediate Similarity	NPC281258
0.7791	Intermediate Similarity	NPC472786
0.7785	Intermediate Similarity	NPC469642
0.7784	Intermediate Similarity	NPC470940
0.7784	Intermediate Similarity	NPC276551
0.7784	Intermediate Similarity	NPC276735

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 NPC474378 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	965
0.2-0.3	2179
0.3-0.4	2667
0.4-0.5	1978
0.5-0.6	770
0.6-0.7	264
0.7-0.8	25
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7927	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD8434	Phase 2
0.7651	Intermediate Similarity	NPD7075	Discontinued
0.7622	Intermediate Similarity	NPD6801	Discontinued
0.7576	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6799	Approved
0.7531	Intermediate Similarity	NPD5403	Approved
0.753	Intermediate Similarity	NPD5402	Approved
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD5401	Approved
0.7394	Intermediate Similarity	NPD6599	Discontinued
0.7381	Intermediate Similarity	NPD3882	Suspended
0.733	Intermediate Similarity	NPD6765	Approved
0.733	Intermediate Similarity	NPD6764	Approved
0.733	Intermediate Similarity	NPD6559	Discontinued
0.7321	Intermediate Similarity	NPD3817	Phase 2
0.7317	Intermediate Similarity	NPD920	Approved
0.7296	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD919	Approved
0.7262	Intermediate Similarity	NPD5760	Phase 2
0.7262	Intermediate Similarity	NPD5761	Phase 2
0.7235	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD9092	Discovery
0.72	Intermediate Similarity	NPD3818	Discontinued
0.7195	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2344	Approved
0.7186	Intermediate Similarity	NPD4380	Phase 2
0.7167	Intermediate Similarity	NPD6785	Approved
0.7167	Intermediate Similarity	NPD6784	Approved
0.7159	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1247	Approved
0.7095	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6166	Phase 2
0.7081	Intermediate Similarity	NPD1471	Phase 3
0.7078	Intermediate Similarity	NPD5647	Approved
0.7076	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7411	Suspended
0.7035	Intermediate Similarity	NPD3749	Approved
0.7029	Intermediate Similarity	NPD3926	Phase 2
0.7024	Intermediate Similarity	NPD3226	Approved
0.7019	Intermediate Similarity	NPD1551	Phase 2
0.7012	Intermediate Similarity	NPD2309	Approved
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD1934	Approved
0.6994	Remote Similarity	NPD1243	Approved
0.6994	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2532	Approved
0.6988	Remote Similarity	NPD2534	Approved
0.6988	Remote Similarity	NPD2533	Approved
0.6983	Remote Similarity	NPD6797	Phase 2
0.6983	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD447	Suspended
0.6981	Remote Similarity	NPD6355	Discontinued
0.6975	Remote Similarity	NPD6004	Phase 3
0.6975	Remote Similarity	NPD6002	Phase 3
0.6975	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6005	Phase 3
0.6975	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7819	Suspended
0.6957	Remote Similarity	NPD2799	Discontinued
0.6944	Remote Similarity	NPD7251	Discontinued
0.6933	Remote Similarity	NPD1549	Phase 2
0.6928	Remote Similarity	NPD9717	Approved
0.6914	Remote Similarity	NPD2796	Approved
0.6909	Remote Similarity	NPD2354	Approved
0.6909	Remote Similarity	NPD6190	Approved
0.6909	Remote Similarity	NPD3887	Approved
0.6906	Remote Similarity	NPD7808	Phase 3
0.6899	Remote Similarity	NPD2313	Discontinued
0.689	Remote Similarity	NPD2800	Approved
0.6885	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8404	Phase 2
0.6879	Remote Similarity	NPD6832	Phase 2
0.6871	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD8313	Approved
0.6868	Remote Similarity	NPD8312	Approved
0.686	Remote Similarity	NPD2801	Approved
0.6857	Remote Similarity	NPD5494	Approved
0.6855	Remote Similarity	NPD6233	Phase 2
0.6851	Remote Similarity	NPD7685	Pre-registration
0.6833	Remote Similarity	NPD7074	Phase 3
0.6829	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6798	Discontinued
0.6786	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3787	Discontinued
0.678	Remote Similarity	NPD6808	Phase 2
0.6778	Remote Similarity	NPD7054	Approved
0.677	Remote Similarity	NPD230	Phase 1
0.676	Remote Similarity	NPD7473	Discontinued
0.6757	Remote Similarity	NPD8150	Discontinued
0.6748	Remote Similarity	NPD1510	Phase 2
0.6746	Remote Similarity	NPD1512	Approved
0.674	Remote Similarity	NPD7472	Approved
0.6728	Remote Similarity	NPD6653	Approved
0.6726	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2163	Approved
0.6711	Remote Similarity	NPD9545	Approved
0.671	Remote Similarity	NPD1608	Approved
0.6708	Remote Similarity	NPD1240	Approved
0.6707	Remote Similarity	NPD2935	Discontinued
0.6704	Remote Similarity	NPD2403	Approved
0.6704	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5953	Discontinued
0.6701	Remote Similarity	NPD7435	Discontinued
0.6688	Remote Similarity	NPD1203	Approved
0.6686	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4965	Approved
0.6686	Remote Similarity	NPD4966	Approved
0.6686	Remote Similarity	NPD4967	Phase 2
0.6685	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7972	Discontinued
0.6667	Remote Similarity	NPD2353	Approved
0.6649	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1019	Discontinued
0.6646	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4062	Phase 3
0.6627	Remote Similarity	NPD1511	Approved
0.6626	Remote Similarity	NPD1607	Approved
0.6625	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6234	Discontinued
0.6608	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD9494	Approved
0.6593	Remote Similarity	NPD5844	Phase 1
0.6591	Remote Similarity	NPD7768	Phase 2
0.6584	Remote Similarity	NPD411	Approved
0.6584	Remote Similarity	NPD3268	Approved
0.6584	Remote Similarity	NPD3764	Approved
0.6584	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5762	Approved
0.6566	Remote Similarity	NPD5763	Approved
0.6564	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5049	Phase 3
0.6548	Remote Similarity	NPD3750	Approved
0.6548	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD6782	Approved
0.6546	Remote Similarity	NPD6776	Approved
0.6546	Remote Similarity	NPD6780	Approved
0.6546	Remote Similarity	NPD6777	Approved
0.6546	Remote Similarity	NPD6781	Approved
0.6546	Remote Similarity	NPD6778	Approved
0.6546	Remote Similarity	NPD6779	Approved
0.6545	Remote Similarity	NPD4308	Phase 3
0.6541	Remote Similarity	NPD2798	Approved
0.6538	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7799	Discontinued
0.6536	Remote Similarity	NPD7199	Phase 2
0.6536	Remote Similarity	NPD6959	Discontinued
0.6534	Remote Similarity	NPD2296	Approved
0.6527	Remote Similarity	NPD5958	Discontinued
0.6527	Remote Similarity	NPD2424	Discontinued
0.6524	Remote Similarity	NPD6651	Approved
0.6519	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD17	Approved
0.6514	Remote Similarity	NPD37	Approved
0.6514	Remote Similarity	NPD6279	Approved
0.6514	Remote Similarity	NPD6280	Approved
0.6503	Remote Similarity	NPD7286	Phase 2
0.65	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7874	Approved
0.6491	Remote Similarity	NPD4661	Approved
0.6491	Remote Similarity	NPD4662	Approved
0.6485	Remote Similarity	NPD7097	Phase 1
0.6481	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD2797	Approved
0.6477	Remote Similarity	NPD1465	Phase 2
0.6471	Remote Similarity	NPD9493	Approved
0.6463	Remote Similarity	NPD1933	Approved
0.6453	Remote Similarity	NPD6273	Approved
0.6448	Remote Similarity	NPD7228	Approved
0.6443	Remote Similarity	NPD2067	Discontinued
0.6442	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7458	Discontinued
0.6429	Remote Similarity	NPD4534	Discontinued
0.6421	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7095	Approved
0.6414	Remote Similarity	NPD8319	Approved
0.6414	Remote Similarity	NPD8320	Phase 1
0.6409	Remote Similarity	NPD5710	Approved
0.6409	Remote Similarity	NPD5711	Approved
0.6402	Remote Similarity	NPD4060	Phase 1
0.6384	Remote Similarity	NPD8455	Phase 2

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