NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	421.19
Volume:	432.03
LogP:	4.439
LogD:	3.746
LogS:	-4.28
# Rotatable Bonds:	1
TPSA:	79.23
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	5.469
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.827
MDCK Permeability:	6.474729161709547e-05
Pgp-inhibitor:	0.061
Pgp-substrate:	0.962
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.389
30% Bioavailability (F30%):	0.096

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	96.04643249511719%
Volume Distribution (VD):	1.631
Pgp-substrate:	4.43324613571167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.311
CYP1A2-substrate:	0.786
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.363
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.351
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	9.979
Half-life (T1/2):	0.425

ADMET: Toxicity

hERG Blockers:	0.682
Human Hepatotoxicity (H-HT):	0.975
Drug-inuced Liver Injury (DILI):	0.909
AMES Toxicity:	0.794
Rat Oral Acute Toxicity:	0.295
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.949
Carcinogencity:	0.243
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC32154

Natural Product ID:	NPC32154
*Common Name:**	Lyfoline
IUPAC Name:	(1S,13Z,17S,19R)-4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.18,12.02,7.019,24]hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one
Synonyms:	Epi-Lyfoline
Standard InCHIKey:	CDTGNBVPXHNHGE-RDOPERODSA-N
Standard InCHI:	InChI=1S/C25H27NO5/c1-30-24-14-18-19(13-23(24)28)21-12-17(11-16-4-2-3-9-26(16)21)31-25(29)8-6-15-5-7-22(27)20(18)10-15/h5-8,10,13-14,16-17,21,27-28H,2-4,9,11-12H2,1H3/b8-6-/t16-,17+,21+/m1/s1
SMILES:	COC1=C(C=C2[C@@H]3C[C@H](C[C@@H]4N3CCCC4)OC(=O)/C=C\C5=CC(=C(C=C5)O)C2=C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	6436825
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000221] Quinolizidines

*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
NPO26661	Heimia salicifolia	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO26661	Heimia salicifolia	Species	Lythraceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.8	ug/ml	PMID[19299148]

☑ 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 NPC32154 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	266
0.1-0.2	1256
0.2-0.3	3679
0.3-0.4	10961
0.4-0.5	7217
0.5-0.6	8649
0.6-0.7	9419
0.7-0.8	1007
0.8-0.85	209
0.85-0.9	32
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC241704
0.8951	High Similarity	NPC276588
0.8951	High Similarity	NPC184026
0.8951	High Similarity	NPC2413
0.8951	High Similarity	NPC469817
0.8951	High Similarity	NPC295691
0.8951	High Similarity	NPC127674
0.8951	High Similarity	NPC249797
0.8951	High Similarity	NPC39701
0.8951	High Similarity	NPC54379
0.8951	High Similarity	NPC278799
0.8951	High Similarity	NPC110416
0.8951	High Similarity	NPC189266
0.8951	High Similarity	NPC193949
0.8951	High Similarity	NPC5238
0.8951	High Similarity	NPC207757
0.8951	High Similarity	NPC204828
0.8951	High Similarity	NPC172765
0.8862	High Similarity	NPC13916
0.8862	High Similarity	NPC264850
0.881	High Similarity	NPC145832
0.881	High Similarity	NPC306555
0.881	High Similarity	NPC205421
0.881	High Similarity	NPC81218
0.881	High Similarity	NPC474931
0.881	High Similarity	NPC158376
0.881	High Similarity	NPC117188
0.881	High Similarity	NPC12053
0.8802	High Similarity	NPC24465
0.8802	High Similarity	NPC196447
0.8802	High Similarity	NPC136508
0.8802	High Similarity	NPC78222
0.8802	High Similarity	NPC477563
0.8802	High Similarity	NPC96603
0.8802	High Similarity	NPC212794
0.8802	High Similarity	NPC253043
0.8802	High Similarity	NPC306843
0.8802	High Similarity	NPC13504
0.8795	High Similarity	NPC60186
0.8743	High Similarity	NPC324144
0.8704	High Similarity	NPC88249
0.8704	High Similarity	NPC97221
0.8704	High Similarity	NPC220858
0.8704	High Similarity	NPC192768
0.8704	High Similarity	NPC151895
0.869	High Similarity	NPC276944
0.869	High Similarity	NPC232514
0.869	High Similarity	NPC238530
0.8642	High Similarity	NPC103379
0.8642	High Similarity	NPC477565
0.8631	High Similarity	NPC1229
0.8623	High Similarity	NPC166014
0.8623	High Similarity	NPC27410
0.8605	High Similarity	NPC2314
0.858	High Similarity	NPC135538
0.858	High Similarity	NPC476571
0.858	High Similarity	NPC24233
0.858	High Similarity	NPC428
0.858	High Similarity	NPC147390
0.858	High Similarity	NPC246587
0.8563	High Similarity	NPC320223
0.8563	High Similarity	NPC114364
0.8555	High Similarity	NPC128560
0.8555	High Similarity	NPC199465
0.8555	High Similarity	NPC229166
0.8547	High Similarity	NPC239775
0.8539	High Similarity	NPC22115
0.8539	High Similarity	NPC275680
0.8538	High Similarity	NPC204908
0.8538	High Similarity	NPC83198
0.8523	High Similarity	NPC116284
0.8519	High Similarity	NPC106295
0.8519	High Similarity	NPC191376
0.8519	High Similarity	NPC210437
0.8519	High Similarity	NPC476144
0.8519	High Similarity	NPC51957
0.8519	High Similarity	NPC16107
0.8519	High Similarity	NPC321505
0.8519	High Similarity	NPC179825
0.8519	High Similarity	NPC476151
0.8514	High Similarity	NPC220961
0.8497	Intermediate Similarity	NPC477020
0.8497	Intermediate Similarity	NPC66341
0.8497	Intermediate Similarity	NPC192135
0.8492	Intermediate Similarity	NPC206900
0.8488	Intermediate Similarity	NPC26240
0.8488	Intermediate Similarity	NPC69712
0.8488	Intermediate Similarity	NPC118274
0.8488	Intermediate Similarity	NPC168753
0.8488	Intermediate Similarity	NPC477562
0.8471	Intermediate Similarity	NPC169743
0.8466	Intermediate Similarity	NPC7467
0.8452	Intermediate Similarity	NPC111485
0.843	Intermediate Similarity	NPC470324
0.8427	Intermediate Similarity	NPC302245
0.8427	Intermediate Similarity	NPC95426
0.8427	Intermediate Similarity	NPC16357
0.8421	Intermediate Similarity	NPC124657
0.8418	Intermediate Similarity	NPC8836
0.8418	Intermediate Similarity	NPC15414
0.8418	Intermediate Similarity	NPC42663
0.8418	Intermediate Similarity	NPC328155
0.8418	Intermediate Similarity	NPC271013
0.8418	Intermediate Similarity	NPC223690
0.8418	Intermediate Similarity	NPC251735
0.8418	Intermediate Similarity	NPC182052
0.8418	Intermediate Similarity	NPC7715
0.8418	Intermediate Similarity	NPC104196
0.8418	Intermediate Similarity	NPC54654
0.8418	Intermediate Similarity	NPC239824
0.8418	Intermediate Similarity	NPC258657
0.8418	Intermediate Similarity	NPC229373
0.8418	Intermediate Similarity	NPC217748
0.8418	Intermediate Similarity	NPC49075
0.8418	Intermediate Similarity	NPC222661
0.8418	Intermediate Similarity	NPC290005
0.8418	Intermediate Similarity	NPC290582
0.8418	Intermediate Similarity	NPC181796
0.8418	Intermediate Similarity	NPC279228
0.8418	Intermediate Similarity	NPC90998
0.8418	Intermediate Similarity	NPC311973
0.8418	Intermediate Similarity	NPC185639
0.8418	Intermediate Similarity	NPC285931
0.8402	Intermediate Similarity	NPC249274
0.8402	Intermediate Similarity	NPC205167
0.84	Intermediate Similarity	NPC237044
0.8395	Intermediate Similarity	NPC185838
0.8393	Intermediate Similarity	NPC476572
0.8391	Intermediate Similarity	NPC190783
0.8391	Intermediate Similarity	NPC232386
0.8391	Intermediate Similarity	NPC152680
0.8383	Intermediate Similarity	NPC325871
0.8383	Intermediate Similarity	NPC99659
0.838	Intermediate Similarity	NPC139783
0.838	Intermediate Similarity	NPC65312
0.8372	Intermediate Similarity	NPC150879
0.8372	Intermediate Similarity	NPC210140
0.8371	Intermediate Similarity	NPC167116
0.8371	Intermediate Similarity	NPC274716
0.8371	Intermediate Similarity	NPC254441
0.8363	Intermediate Similarity	NPC3375
0.8363	Intermediate Similarity	NPC255607
0.8362	Intermediate Similarity	NPC286119
0.8352	Intermediate Similarity	NPC474325
0.8343	Intermediate Similarity	NPC304675
0.8323	Intermediate Similarity	NPC2295
0.8323	Intermediate Similarity	NPC477564
0.8315	Intermediate Similarity	NPC248642
0.8315	Intermediate Similarity	NPC30779
0.8314	Intermediate Similarity	NPC81247
0.8314	Intermediate Similarity	NPC250846
0.8314	Intermediate Similarity	NPC268503
0.8314	Intermediate Similarity	NPC240841
0.8314	Intermediate Similarity	NPC476573
0.8314	Intermediate Similarity	NPC35627
0.8314	Intermediate Similarity	NPC317272
0.8314	Intermediate Similarity	NPC42549
0.8314	Intermediate Similarity	NPC256012
0.8305	Intermediate Similarity	NPC126284
0.8305	Intermediate Similarity	NPC474745
0.8305	Intermediate Similarity	NPC474507
0.8297	Intermediate Similarity	NPC478093
0.8287	Intermediate Similarity	NPC82763
0.8278	Intermediate Similarity	NPC212237
0.8278	Intermediate Similarity	NPC116465
0.8274	Intermediate Similarity	NPC216459
0.8274	Intermediate Similarity	NPC138487
0.8274	Intermediate Similarity	NPC41178
0.8272	Intermediate Similarity	NPC476567
0.8272	Intermediate Similarity	NPC128019
0.8272	Intermediate Similarity	NPC136860
0.8268	Intermediate Similarity	NPC156576
0.8268	Intermediate Similarity	NPC135772
0.8266	Intermediate Similarity	NPC298979
0.8263	Intermediate Similarity	NPC133011
0.8263	Intermediate Similarity	NPC82285
0.8258	Intermediate Similarity	NPC312918
0.8258	Intermediate Similarity	NPC476574
0.8258	Intermediate Similarity	NPC155442
0.8258	Intermediate Similarity	NPC477561
0.8256	Intermediate Similarity	NPC134858
0.8251	Intermediate Similarity	NPC478091
0.8251	Intermediate Similarity	NPC478092
0.8251	Intermediate Similarity	NPC30182
0.8251	Intermediate Similarity	NPC473589
0.8249	Intermediate Similarity	NPC118633
0.8249	Intermediate Similarity	NPC148693
0.8249	Intermediate Similarity	NPC294790
0.8232	Intermediate Similarity	NPC237579
0.8225	Intermediate Similarity	NPC146288
0.8225	Intermediate Similarity	NPC147091
0.8225	Intermediate Similarity	NPC186063
0.8208	Intermediate Similarity	NPC24264
0.8208	Intermediate Similarity	NPC476432
0.8204	Intermediate Similarity	NPC326316
0.8204	Intermediate Similarity	NPC81733
0.8204	Intermediate Similarity	NPC277669
0.8204	Intermediate Similarity	NPC476579
0.8204	Intermediate Similarity	NPC76213
0.8198	Intermediate Similarity	NPC233650

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 NPC32154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	643
0.2-0.3	931
0.3-0.4	2042
0.4-0.5	2531
0.5-0.6	1804
0.6-0.7	831
0.7-0.8	172
0.8-0.85	18
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD4584	Approved
0.843	Intermediate Similarity	NPD2898	Approved
0.8418	Intermediate Similarity	NPD8054	Approved
0.8418	Intermediate Similarity	NPD8053	Approved
0.8148	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD2489	Approved
0.8114	Intermediate Similarity	NPD27	Approved
0.8114	Intermediate Similarity	NPD4481	Phase 3
0.8107	Intermediate Similarity	NPD4773	Phase 2
0.8107	Intermediate Similarity	NPD4772	Phase 2
0.8079	Intermediate Similarity	NPD8156	Discontinued
0.8057	Intermediate Similarity	NPD2970	Approved
0.8057	Intermediate Similarity	NPD2969	Approved
0.8046	Intermediate Similarity	NPD6107	Approved
0.8023	Intermediate Similarity	NPD8099	Discontinued
0.8023	Intermediate Similarity	NPD8252	Approved
0.8023	Intermediate Similarity	NPD8251	Approved
0.8	Intermediate Similarity	NPD3051	Approved
0.7914	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD2421	Approved
0.7904	Intermediate Similarity	NPD2420	Approved
0.788	Intermediate Similarity	NPD7906	Approved
0.7857	Intermediate Similarity	NPD7310	Approved
0.7857	Intermediate Similarity	NPD7311	Approved
0.7857	Intermediate Similarity	NPD7313	Approved
0.7857	Intermediate Similarity	NPD7312	Approved
0.7857	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7309	Approved
0.7797	Intermediate Similarity	NPD6071	Discontinued
0.7797	Intermediate Similarity	NPD4010	Discontinued
0.7778	Intermediate Similarity	NPD5313	Approved
0.7778	Intermediate Similarity	NPD5312	Approved
0.7765	Intermediate Similarity	NPD3640	Phase 3
0.7765	Intermediate Similarity	NPD3639	Approved
0.7765	Intermediate Similarity	NPD3641	Approved
0.776	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD4578	Approved
0.776	Intermediate Similarity	NPD4577	Approved
0.7759	Intermediate Similarity	NPD2560	Approved
0.7759	Intermediate Similarity	NPD2563	Approved
0.7746	Intermediate Similarity	NPD7298	Approved
0.7737	Intermediate Similarity	NPD4420	Approved
0.773	Intermediate Similarity	NPD4663	Approved
0.7705	Intermediate Similarity	NPD7549	Discontinued
0.7701	Intermediate Similarity	NPD2488	Approved
0.7701	Intermediate Similarity	NPD2490	Approved
0.7684	Intermediate Similarity	NPD4666	Phase 3
0.7679	Intermediate Similarity	NPD5241	Discontinued
0.767	Intermediate Similarity	NPD7833	Phase 2
0.767	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7831	Phase 2
0.7668	Intermediate Similarity	NPD5005	Approved
0.7668	Intermediate Similarity	NPD5006	Approved
0.7636	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6667	Approved
0.7633	Intermediate Similarity	NPD6666	Approved
0.7633	Intermediate Similarity	NPD3845	Phase 1
0.7627	Intermediate Similarity	NPD5709	Phase 3
0.7622	Intermediate Similarity	NPD6853	Approved
0.7622	Intermediate Similarity	NPD6851	Approved
0.7614	Intermediate Similarity	NPD6788	Approved
0.7596	Intermediate Similarity	NPD6297	Approved
0.7584	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4017	Approved
0.7558	Intermediate Similarity	NPD6030	Approved
0.7558	Intermediate Similarity	NPD6031	Approved
0.7526	Intermediate Similarity	NPD3452	Approved
0.7526	Intermediate Similarity	NPD2494	Approved
0.7526	Intermediate Similarity	NPD3450	Approved
0.7526	Intermediate Similarity	NPD2493	Approved
0.7514	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6386	Approved
0.7486	Intermediate Similarity	NPD6385	Approved
0.7475	Intermediate Similarity	NPD7047	Phase 3
0.7427	Intermediate Similarity	NPD6997	Phase 2
0.7416	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD4582	Approved
0.7411	Intermediate Similarity	NPD4583	Approved
0.7401	Intermediate Similarity	NPD2977	Approved
0.7401	Intermediate Similarity	NPD2978	Approved
0.7398	Intermediate Similarity	NPD3448	Approved
0.7398	Intermediate Similarity	NPD2491	Approved
0.7398	Intermediate Similarity	NPD3057	Approved
0.7385	Intermediate Similarity	NPD4107	Approved
0.7381	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD2971	Approved
0.738	Intermediate Similarity	NPD2968	Approved
0.736	Intermediate Similarity	NPD4002	Approved
0.736	Intermediate Similarity	NPD4004	Approved
0.7353	Intermediate Similarity	NPD4236	Phase 3
0.7353	Intermediate Similarity	NPD4237	Approved
0.7353	Intermediate Similarity	NPD3060	Approved
0.7353	Intermediate Similarity	NPD5177	Phase 3
0.734	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7177	Discontinued
0.7337	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2975	Approved
0.732	Intermediate Similarity	NPD2974	Approved
0.732	Intermediate Similarity	NPD2973	Approved
0.731	Intermediate Similarity	NPD3533	Approved
0.731	Intermediate Similarity	NPD2972	Approved
0.7299	Intermediate Similarity	NPD6090	Discontinued
0.7299	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6042	Phase 2
0.7297	Intermediate Similarity	NPD42	Phase 2
0.7293	Intermediate Similarity	NPD5677	Discontinued
0.7278	Intermediate Similarity	NPD4055	Discovery
0.7277	Intermediate Similarity	NPD5676	Approved
0.7273	Intermediate Similarity	NPD7039	Approved
0.7273	Intermediate Similarity	NPD7038	Approved
0.7268	Intermediate Similarity	NPD5242	Approved
0.7267	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5977	Approved
0.7263	Intermediate Similarity	NPD5978	Approved
0.7259	Intermediate Similarity	NPD4482	Phase 3
0.7257	Intermediate Similarity	NPD1914	Approved
0.7257	Intermediate Similarity	NPD7427	Discontinued
0.7247	Intermediate Similarity	NPD4433	Discontinued
0.7247	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD8095	Phase 1
0.7245	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4040	Phase 1
0.7235	Intermediate Similarity	NPD3656	Approved
0.7229	Intermediate Similarity	NPD4475	Approved
0.7229	Intermediate Similarity	NPD4474	Approved
0.7225	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7291	Discontinued
0.7219	Intermediate Similarity	NPD1753	Discontinued
0.7216	Intermediate Similarity	NPD3687	Approved
0.7216	Intermediate Similarity	NPD3686	Approved
0.7213	Intermediate Similarity	NPD4166	Phase 2
0.7208	Intermediate Similarity	NPD4580	Approved
0.7208	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5773	Approved
0.7207	Intermediate Similarity	NPD5772	Approved
0.7198	Intermediate Similarity	NPD2904	Discontinued
0.7196	Intermediate Similarity	NPD7280	Phase 3
0.7196	Intermediate Similarity	NPD7281	Phase 3
0.7188	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3124	Discontinued
0.7182	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD3455	Phase 2
0.7175	Intermediate Similarity	NPD824	Approved
0.7174	Intermediate Similarity	NPD2388	Discontinued
0.7169	Intermediate Similarity	NPD5718	Phase 2
0.7168	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2122	Discontinued
0.7158	Intermediate Similarity	NPD6618	Phase 2
0.7152	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4162	Approved
0.7143	Intermediate Similarity	NPD4123	Phase 3
0.7143	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1424	Approved
0.7143	Intermediate Similarity	NPD3536	Discontinued
0.7129	Intermediate Similarity	NPD7907	Approved
0.7128	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2674	Phase 3
0.712	Intermediate Similarity	NPD6747	Phase 1
0.7119	Intermediate Similarity	NPD4210	Discontinued
0.7111	Intermediate Similarity	NPD4585	Approved
0.7108	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7497	Discontinued
0.7097	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6873	Phase 2
0.7095	Intermediate Similarity	NPD5089	Approved
0.7095	Intermediate Similarity	NPD6072	Discontinued
0.7095	Intermediate Similarity	NPD5090	Approved
0.7092	Intermediate Similarity	NPD5582	Discontinued
0.7086	Intermediate Similarity	NPD7598	Phase 2
0.7083	Intermediate Similarity	NPD2238	Phase 2
0.7083	Intermediate Similarity	NPD4060	Phase 1
0.7079	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4005	Discontinued
0.7073	Intermediate Similarity	NPD7827	Phase 1
0.7069	Intermediate Similarity	NPD2677	Approved
0.7065	Intermediate Similarity	NPD7802	Discontinued
0.7062	Intermediate Similarity	NPD5976	Discontinued
0.7056	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7400	Phase 3
0.7039	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7266	Discontinued
0.7033	Intermediate Similarity	NPD4665	Approved
0.7033	Intermediate Similarity	NPD4111	Phase 1
0.7031	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7296	Approved
0.7021	Intermediate Similarity	NPD4873	Discontinued
0.7021	Intermediate Similarity	NPD5844	Phase 1
0.7011	Intermediate Similarity	NPD6331	Phase 2
0.7011	Intermediate Similarity	NPD6748	Discontinued
0.701	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7213	Phase 3

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