NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	538.28
Volume:	547.815
LogP:	2.383
LogD:	0.975
LogS:	-2.858
# Rotatable Bonds:	13
TPSA:	142.5
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.264
Synthetic Accessibility Score:	5.037
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
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:	-5.291
MDCK Permeability:	8.278580207843333e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.411
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.877

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.788
Plasma Protein Binding (PPB):	39.73589324951172%
Volume Distribution (VD):	1.012
Pgp-substrate:	45.70701599121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.344
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.546
CYP3A4-substrate:	0.54

ADMET: Excretion

Clearance (CL):	2.207
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.428
Drug-inuced Liver Injury (DILI):	0.844
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.816
Maximum Recommended Daily Dose:	0.22
Skin Sensitization:	0.044
Carcinogencity:	0.241
Eye Corrosion:	0.812
Eye Irritation:	0.273
Respiratory Toxicity:	0.482

Download Data

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

Natural Product: NPC477439

Natural Product ID:	NPC477439
*Common Name:**	[5-[(4S,4aR,5S,6R,8aS)-4,6-diacetyloxy-5-(acetyloxymethyl)-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]-3-hydroxy-3-methylpentyl] acetate
IUPAC Name:	[5-[(4S,4aR,5S,6R,8aS)-4,6-diacetyloxy-5-(acetyloxymethyl)-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]-3-hydroxy-3-methylpentyl] acetate
Synonyms:
Standard InCHIKey:	WZQVRGPPHJPVQI-CQXIVQJKSA-N
Standard InCHI:	InChI=1S/C28H42O10/c1-16-21(9-11-26(6,34)13-14-35-17(2)29)27(7)12-10-22(37-19(4)31)28(8,15-36-18(3)30)25(27)24(23(16)33)38-20(5)32/h22,24-25,34H,9-15H2,1-8H3/t22-,24-,25-,26?,27-,28+/m1/s1
SMILES:	CC1=C([C@]2(CC[C@H]([C@]([C@@H]2[C@@H](C1=O)OC(=O)C)(C)COC(=O)C)OC(=O)C)C)CCC(C)(CCOC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122187009
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO33600	Leonurus macranthus	Species	Lamiaceae	Eukaryota	aerial parts	Huanren, Liaoning Province, China	2013-AUG	PMID[26348503]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	12700	nM	PMID[26348503]

☑ 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 NPC477439 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	230
0.1-0.2	1492
0.2-0.3	5345
0.3-0.4	9607
0.4-0.5	12208
0.5-0.6	6965
0.6-0.7	5447
0.7-0.8	1359
0.8-0.85	38
0.85-0.9	1
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC477437
0.9886	High Similarity	NPC477438
0.9659	High Similarity	NPC477436
0.9659	High Similarity	NPC477435
0.871	High Similarity	NPC212812
0.8696	High Similarity	NPC248913
0.8646	High Similarity	NPC472972
0.8571	High Similarity	NPC33973
0.8571	High Similarity	NPC70967
0.8557	High Similarity	NPC124211
0.8485	Intermediate Similarity	NPC65523
0.8485	Intermediate Similarity	NPC135854
0.8485	Intermediate Similarity	NPC470251
0.8485	Intermediate Similarity	NPC2436
0.8485	Intermediate Similarity	NPC216245
0.8469	Intermediate Similarity	NPC53222
0.8384	Intermediate Similarity	NPC179208
0.837	Intermediate Similarity	NPC475001
0.837	Intermediate Similarity	NPC185059
0.8333	Intermediate Similarity	NPC305483
0.8333	Intermediate Similarity	NPC328162
0.8333	Intermediate Similarity	NPC96859
0.8317	Intermediate Similarity	NPC44063
0.8286	Intermediate Similarity	NPC473798
0.8283	Intermediate Similarity	NPC308726
0.8283	Intermediate Similarity	NPC119601
0.8283	Intermediate Similarity	NPC80781
0.8269	Intermediate Similarity	NPC90769
0.8265	Intermediate Similarity	NPC157787
0.8265	Intermediate Similarity	NPC88198
0.8247	Intermediate Similarity	NPC216904
0.8247	Intermediate Similarity	NPC285513
0.8235	Intermediate Similarity	NPC94942
0.8235	Intermediate Similarity	NPC476479
0.8235	Intermediate Similarity	NPC293850
0.8229	Intermediate Similarity	NPC470016
0.8229	Intermediate Similarity	NPC134067
0.8229	Intermediate Similarity	NPC317586
0.8218	Intermediate Similarity	NPC472645
0.8208	Intermediate Similarity	NPC96312
0.8208	Intermediate Similarity	NPC328374
0.8208	Intermediate Similarity	NPC134869
0.8208	Intermediate Similarity	NPC152199
0.8208	Intermediate Similarity	NPC235539
0.8208	Intermediate Similarity	NPC251236
0.8208	Intermediate Similarity	NPC40632
0.8182	Intermediate Similarity	NPC163372
0.8182	Intermediate Similarity	NPC302537
0.8182	Intermediate Similarity	NPC472643
0.8182	Intermediate Similarity	NPC469327
0.8163	Intermediate Similarity	NPC112753
0.8163	Intermediate Similarity	NPC275439
0.8155	Intermediate Similarity	NPC2766
0.8155	Intermediate Similarity	NPC77947
0.8155	Intermediate Similarity	NPC286174
0.8152	Intermediate Similarity	NPC475181
0.8125	Intermediate Similarity	NPC272635
0.8125	Intermediate Similarity	NPC169751
0.8125	Intermediate Similarity	NPC293086
0.8125	Intermediate Similarity	NPC166906
0.8125	Intermediate Similarity	NPC240617
0.8119	Intermediate Similarity	NPC118911
0.8113	Intermediate Similarity	NPC18547
0.8113	Intermediate Similarity	NPC474906
0.8105	Intermediate Similarity	NPC235704
0.8105	Intermediate Similarity	NPC99380
0.8095	Intermediate Similarity	NPC474516
0.8077	Intermediate Similarity	NPC272898
0.8077	Intermediate Similarity	NPC129689
0.8077	Intermediate Similarity	NPC473036
0.8061	Intermediate Similarity	NPC254496
0.8061	Intermediate Similarity	NPC43747
0.8061	Intermediate Similarity	NPC473456
0.8056	Intermediate Similarity	NPC297179
0.8041	Intermediate Similarity	NPC139570
0.8039	Intermediate Similarity	NPC1679
0.8039	Intermediate Similarity	NPC181357
0.8037	Intermediate Similarity	NPC16081
0.8037	Intermediate Similarity	NPC173686
0.8022	Intermediate Similarity	NPC64600
0.8021	Intermediate Similarity	NPC79117
0.8021	Intermediate Similarity	NPC109414
0.8021	Intermediate Similarity	NPC271652
0.802	Intermediate Similarity	NPC275583
0.8019	Intermediate Similarity	NPC208998
0.8019	Intermediate Similarity	NPC159333
0.8019	Intermediate Similarity	NPC198539
0.8019	Intermediate Similarity	NPC7921
0.8019	Intermediate Similarity	NPC49451
0.8	Intermediate Similarity	NPC171888
0.8	Intermediate Similarity	NPC146945
0.8	Intermediate Similarity	NPC34315
0.8	Intermediate Similarity	NPC115303
0.8	Intermediate Similarity	NPC43775
0.7981	Intermediate Similarity	NPC41405
0.7979	Intermediate Similarity	NPC230387
0.7961	Intermediate Similarity	NPC144854
0.7961	Intermediate Similarity	NPC3316
0.7959	Intermediate Similarity	NPC95565
0.7959	Intermediate Similarity	NPC471822
0.7959	Intermediate Similarity	NPC62516
0.7959	Intermediate Similarity	NPC157113
0.7957	Intermediate Similarity	NPC229717
0.7957	Intermediate Similarity	NPC73038
0.7944	Intermediate Similarity	NPC45218
0.7944	Intermediate Similarity	NPC268238
0.7944	Intermediate Similarity	NPC143268
0.7944	Intermediate Similarity	NPC323821
0.7941	Intermediate Similarity	NPC213366
0.7941	Intermediate Similarity	NPC40170
0.7938	Intermediate Similarity	NPC184870
0.7938	Intermediate Similarity	NPC74751
0.7935	Intermediate Similarity	NPC120158
0.7935	Intermediate Similarity	NPC475193
0.7925	Intermediate Similarity	NPC147180
0.7925	Intermediate Similarity	NPC11252
0.7925	Intermediate Similarity	NPC289312
0.7925	Intermediate Similarity	NPC193948
0.7921	Intermediate Similarity	NPC136289
0.7921	Intermediate Similarity	NPC295791
0.7921	Intermediate Similarity	NPC22388
0.79	Intermediate Similarity	NPC472644
0.79	Intermediate Similarity	NPC316964
0.79	Intermediate Similarity	NPC476274
0.79	Intermediate Similarity	NPC46761
0.79	Intermediate Similarity	NPC198880
0.79	Intermediate Similarity	NPC293890
0.789	Intermediate Similarity	NPC17772
0.7885	Intermediate Similarity	NPC469916
0.7885	Intermediate Similarity	NPC154608
0.7885	Intermediate Similarity	NPC192813
0.7885	Intermediate Similarity	NPC277017
0.7885	Intermediate Similarity	NPC322903
0.7885	Intermediate Similarity	NPC472439
0.7879	Intermediate Similarity	NPC121402
0.7879	Intermediate Similarity	NPC38530
0.7879	Intermediate Similarity	NPC132753
0.7879	Intermediate Similarity	NPC224356
0.7879	Intermediate Similarity	NPC175351
0.7879	Intermediate Similarity	NPC170131
0.7879	Intermediate Similarity	NPC18319
0.7879	Intermediate Similarity	NPC84335
0.7879	Intermediate Similarity	NPC151681
0.7879	Intermediate Similarity	NPC26413
0.7879	Intermediate Similarity	NPC18509
0.7879	Intermediate Similarity	NPC23680
0.787	Intermediate Similarity	NPC270958
0.7864	Intermediate Similarity	NPC51452
0.7864	Intermediate Similarity	NPC475494
0.7864	Intermediate Similarity	NPC111952
0.7857	Intermediate Similarity	NPC30677
0.7857	Intermediate Similarity	NPC255809
0.7857	Intermediate Similarity	NPC37787
0.7857	Intermediate Similarity	NPC473415
0.7857	Intermediate Similarity	NPC473170
0.7857	Intermediate Similarity	NPC469329
0.7857	Intermediate Similarity	NPC180557
0.785	Intermediate Similarity	NPC472926
0.785	Intermediate Similarity	NPC471204
0.785	Intermediate Similarity	NPC202889
0.785	Intermediate Similarity	NPC25909
0.785	Intermediate Similarity	NPC194100
0.7849	Intermediate Similarity	NPC90287
0.7849	Intermediate Similarity	NPC197823
0.7849	Intermediate Similarity	NPC478245
0.7849	Intermediate Similarity	NPC474680
0.7843	Intermediate Similarity	NPC264048
0.7843	Intermediate Similarity	NPC251017
0.7843	Intermediate Similarity	NPC90177
0.7835	Intermediate Similarity	NPC295643
0.7835	Intermediate Similarity	NPC272075
0.7835	Intermediate Similarity	NPC214756
0.783	Intermediate Similarity	NPC201992
0.7826	Intermediate Similarity	NPC476100
0.7822	Intermediate Similarity	NPC81530
0.7822	Intermediate Similarity	NPC118964
0.7822	Intermediate Similarity	NPC224720
0.7822	Intermediate Similarity	NPC476240
0.7822	Intermediate Similarity	NPC476223
0.7822	Intermediate Similarity	NPC115862
0.7818	Intermediate Similarity	NPC472933
0.7818	Intermediate Similarity	NPC470777
0.7812	Intermediate Similarity	NPC134321
0.7812	Intermediate Similarity	NPC20388
0.7812	Intermediate Similarity	NPC475823
0.7812	Intermediate Similarity	NPC128672
0.7812	Intermediate Similarity	NPC113393
0.7812	Intermediate Similarity	NPC474728
0.7812	Intermediate Similarity	NPC474209
0.781	Intermediate Similarity	NPC27814
0.7802	Intermediate Similarity	NPC473420
0.7802	Intermediate Similarity	NPC327002
0.78	Intermediate Similarity	NPC58942
0.78	Intermediate Similarity	NPC478056
0.78	Intermediate Similarity	NPC260149
0.78	Intermediate Similarity	NPC264378
0.7798	Intermediate Similarity	NPC97908
0.7798	Intermediate Similarity	NPC122033
0.7798	Intermediate Similarity	NPC470854
0.7798	Intermediate Similarity	NPC309433

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 NPC477439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	2049
0.2-0.3	3710
0.3-0.4	2019
0.4-0.5	708
0.5-0.6	232
0.6-0.7	142
0.7-0.8	73
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8586	High Similarity	NPD6675	Approved
0.8586	High Similarity	NPD5739	Approved
0.8586	High Similarity	NPD6402	Approved
0.8586	High Similarity	NPD7128	Approved
0.8515	High Similarity	NPD6373	Approved
0.8515	High Similarity	NPD6372	Approved
0.8416	Intermediate Similarity	NPD6899	Approved
0.8416	Intermediate Similarity	NPD7320	Approved
0.8416	Intermediate Similarity	NPD6881	Approved
0.835	Intermediate Similarity	NPD6650	Approved
0.835	Intermediate Similarity	NPD6649	Approved
0.8317	Intermediate Similarity	NPD5697	Approved
0.8317	Intermediate Similarity	NPD5701	Approved
0.8269	Intermediate Similarity	NPD6882	Approved
0.8269	Intermediate Similarity	NPD8297	Approved
0.8252	Intermediate Similarity	NPD7290	Approved
0.8252	Intermediate Similarity	NPD6883	Approved
0.8252	Intermediate Similarity	NPD7102	Approved
0.8173	Intermediate Similarity	NPD6869	Approved
0.8173	Intermediate Similarity	NPD8130	Phase 1
0.8173	Intermediate Similarity	NPD6847	Approved
0.8173	Intermediate Similarity	NPD6617	Approved
0.8155	Intermediate Similarity	NPD6012	Approved
0.8155	Intermediate Similarity	NPD6013	Approved
0.8155	Intermediate Similarity	NPD6014	Approved
0.8058	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7748	Approved
0.7879	Intermediate Similarity	NPD4755	Approved
0.7879	Intermediate Similarity	NPD6084	Phase 2
0.7879	Intermediate Similarity	NPD7902	Approved
0.7879	Intermediate Similarity	NPD6083	Phase 2
0.7857	Intermediate Similarity	NPD5695	Phase 3
0.7732	Intermediate Similarity	NPD7515	Phase 2
0.7723	Intermediate Similarity	NPD5285	Approved
0.7723	Intermediate Similarity	NPD5286	Approved
0.7723	Intermediate Similarity	NPD4700	Approved
0.7723	Intermediate Similarity	NPD4696	Approved
0.7706	Intermediate Similarity	NPD6274	Approved
0.7658	Intermediate Similarity	NPD7101	Approved
0.7658	Intermediate Similarity	NPD7100	Approved
0.7653	Intermediate Similarity	NPD6399	Phase 3
0.7624	Intermediate Similarity	NPD5696	Approved
0.7604	Intermediate Similarity	NPD5737	Approved
0.7604	Intermediate Similarity	NPD6672	Approved
0.7589	Intermediate Similarity	NPD6319	Approved
0.7576	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7900	Approved
0.7573	Intermediate Similarity	NPD5226	Approved
0.7573	Intermediate Similarity	NPD4633	Approved
0.7573	Intermediate Similarity	NPD5211	Phase 2
0.7573	Intermediate Similarity	NPD5225	Approved
0.7573	Intermediate Similarity	NPD5224	Approved
0.7568	Intermediate Similarity	NPD6335	Approved
0.7526	Intermediate Similarity	NPD5328	Approved
0.7524	Intermediate Similarity	NPD4768	Approved
0.7524	Intermediate Similarity	NPD4767	Approved
0.7522	Intermediate Similarity	NPD6909	Approved
0.7522	Intermediate Similarity	NPD6908	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.7477	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6317	Approved
0.7476	Intermediate Similarity	NPD5223	Approved
0.7429	Intermediate Similarity	NPD5141	Approved
0.7426	Intermediate Similarity	NPD5222	Approved
0.7426	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4697	Phase 3
0.7426	Intermediate Similarity	NPD5221	Approved
0.7411	Intermediate Similarity	NPD6313	Approved
0.7411	Intermediate Similarity	NPD6314	Approved
0.7391	Intermediate Similarity	NPD8328	Phase 3
0.7387	Intermediate Similarity	NPD6868	Approved
0.7383	Intermediate Similarity	NPD4729	Approved
0.7383	Intermediate Similarity	NPD4730	Approved
0.7374	Intermediate Similarity	NPD6079	Approved
0.7374	Intermediate Similarity	NPD6411	Approved
0.7364	Intermediate Similarity	NPD4632	Approved
0.7358	Intermediate Similarity	NPD6008	Approved
0.7353	Intermediate Similarity	NPD5173	Approved
0.7347	Intermediate Similarity	NPD6673	Approved
0.7347	Intermediate Similarity	NPD6080	Approved
0.7347	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6904	Approved
0.7333	Intermediate Similarity	NPD4754	Approved
0.7328	Intermediate Similarity	NPD7492	Approved
0.7321	Intermediate Similarity	NPD6009	Approved
0.7281	Intermediate Similarity	NPD6059	Approved
0.7281	Intermediate Similarity	NPD6054	Approved
0.7265	Intermediate Similarity	NPD6616	Approved
0.7248	Intermediate Similarity	NPD5247	Approved
0.7248	Intermediate Similarity	NPD5251	Approved
0.7248	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5250	Approved
0.7248	Intermediate Similarity	NPD5249	Phase 3
0.7248	Intermediate Similarity	NPD5248	Approved
0.7241	Intermediate Similarity	NPD7604	Phase 2
0.7222	Intermediate Similarity	NPD5128	Approved
0.7217	Intermediate Similarity	NPD5983	Phase 2
0.7216	Intermediate Similarity	NPD3618	Phase 1
0.7216	Intermediate Similarity	NPD6409	Approved
0.7216	Intermediate Similarity	NPD7146	Approved
0.7216	Intermediate Similarity	NPD5330	Approved
0.7216	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD7334	Approved
0.7216	Intermediate Similarity	NPD6684	Approved
0.7203	Intermediate Similarity	NPD7078	Approved
0.7203	Intermediate Similarity	NPD8293	Discontinued
0.72	Intermediate Similarity	NPD6050	Approved
0.7172	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4753	Phase 2
0.7172	Intermediate Similarity	NPD6101	Approved
0.7156	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD7736	Approved
0.7129	Intermediate Similarity	NPD4202	Approved
0.7128	Intermediate Similarity	NPD4695	Discontinued
0.7119	Intermediate Similarity	NPD6336	Discontinued
0.71	Intermediate Similarity	NPD5692	Phase 3
0.7097	Intermediate Similarity	NPD3617	Approved
0.7091	Intermediate Similarity	NPD4634	Approved
0.7071	Intermediate Similarity	NPD6903	Approved
0.7071	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6015	Approved
0.7069	Intermediate Similarity	NPD6016	Approved
0.7069	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6098	Approved
0.703	Intermediate Similarity	NPD5694	Approved
0.703	Intermediate Similarity	NPD5693	Phase 1
0.703	Intermediate Similarity	NPD8035	Phase 2
0.703	Intermediate Similarity	NPD8034	Phase 2
0.7027	Intermediate Similarity	NPD5217	Approved
0.7027	Intermediate Similarity	NPD5215	Approved
0.7027	Intermediate Similarity	NPD5216	Approved
0.7018	Intermediate Similarity	NPD7115	Discovery
0.701	Intermediate Similarity	NPD4786	Approved
0.7009	Intermediate Similarity	NPD5988	Approved
0.699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3667	Approved
0.6972	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5778	Approved
0.6961	Remote Similarity	NPD5779	Approved
0.6952	Remote Similarity	NPD7638	Approved
0.6939	Remote Similarity	NPD1694	Approved
0.6939	Remote Similarity	NPD5329	Approved
0.6937	Remote Similarity	NPD5169	Approved
0.6937	Remote Similarity	NPD5135	Approved
0.6937	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7341	Phase 2
0.6887	Remote Similarity	NPD7639	Approved
0.6887	Remote Similarity	NPD7640	Approved
0.6875	Remote Similarity	NPD5127	Approved
0.6869	Remote Similarity	NPD5279	Phase 3
0.6869	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5281	Approved
0.6863	Remote Similarity	NPD5284	Approved
0.6837	Remote Similarity	NPD3666	Approved
0.6837	Remote Similarity	NPD3133	Approved
0.6837	Remote Similarity	NPD3665	Phase 1
0.6837	Remote Similarity	NPD4197	Approved
0.6827	Remote Similarity	NPD5210	Approved
0.6827	Remote Similarity	NPD4629	Approved
0.6827	Remote Similarity	NPD5654	Approved
0.6792	Remote Similarity	NPD4225	Approved
0.6771	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7632	Discontinued
0.6757	Remote Similarity	NPD5168	Approved
0.6731	Remote Similarity	NPD5282	Discontinued
0.6721	Remote Similarity	NPD6033	Approved
0.67	Remote Similarity	NPD5280	Approved
0.67	Remote Similarity	NPD4694	Approved
0.67	Remote Similarity	NPD5690	Phase 2
0.6698	Remote Similarity	NPD5959	Approved
0.6696	Remote Similarity	NPD5167	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3668	Phase 3
0.6633	Remote Similarity	NPD6435	Approved
0.6633	Remote Similarity	NPD4221	Approved
0.6633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4223	Phase 3
0.6632	Remote Similarity	NPD6116	Phase 1
0.6607	Remote Similarity	NPD6686	Approved
0.6604	Remote Similarity	NPD7614	Phase 1
0.66	Remote Similarity	NPD1696	Phase 3
0.6571	Remote Similarity	NPD6001	Approved
0.6569	Remote Similarity	NPD5208	Approved
0.6532	Remote Similarity	NPD7319	Approved
0.6526	Remote Similarity	NPD6117	Approved
0.65	Remote Similarity	NPD6921	Approved
0.6495	Remote Similarity	NPD7645	Phase 2
0.6449	Remote Similarity	NPD7732	Phase 3
0.6444	Remote Similarity	NPD3704	Approved
0.6444	Remote Similarity	NPD7331	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