NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	412.25
Volume:	425.577
LogP:	1.087
LogD:	0.732
LogS:	-3.454
# Rotatable Bonds:	8
TPSA:	121.13
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	4.913
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.021
MDCK Permeability:	1.550749766465742e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.632
Plasma Protein Binding (PPB):	57.96648025512695%
Volume Distribution (VD):	0.452
Pgp-substrate:	36.71256637573242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.63
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.687
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.306
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	2.722
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.199
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.082
Carcinogencity:	0.009
Eye Corrosion:	0.004
Eye Irritation:	0.041
Respiratory Toxicity:	0.388

Download Data

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

Natural Product: NPC477435

Natural Product ID:	NPC477435
*Common Name:**	[(1S,2R,4aS,8S,8aR)-5-(3,5-dihydroxy-3-methylpentyl)-2,8-dihydroxy-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]methyl acetate
IUPAC Name:	[(1S,2R,4aS,8S,8aR)-5-(3,5-dihydroxy-3-methylpentyl)-2,8-dihydroxy-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]methyl acetate
Synonyms:
Standard InCHIKey:	CCKUOYDCCGWXEK-PZYGZVTGSA-N
Standard InCHI:	InChI=1S/C22H36O7/c1-13-15(6-8-20(3,28)10-11-23)21(4)9-7-16(25)22(5,12-29-14(2)24)19(21)18(27)17(13)26/h16,18-19,23,25,27-28H,6-12H2,1-5H3/t16-,18-,19-,20?,21-,22+/m1/s1
SMILES:	CC1=C([C@]2(CC[C@H]([C@]([C@@H]2[C@@H](C1=O)O)(C)COC(=O)C)O)C)CCC(C)(CCO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122187008
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	=	53600	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 NPC477435 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	222
0.1-0.2	1450
0.2-0.3	5093
0.3-0.4	9685
0.4-0.5	11992
0.5-0.6	6821
0.6-0.7	5516
0.7-0.8	1847
0.8-0.85	62
0.85-0.9	4
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477436
0.9773	High Similarity	NPC477438
0.9773	High Similarity	NPC477437
0.9659	High Similarity	NPC477439
0.8737	High Similarity	NPC472972
0.8617	High Similarity	NPC305483
0.8617	High Similarity	NPC328162
0.8617	High Similarity	NPC96859
0.8602	High Similarity	NPC212812
0.8587	High Similarity	NPC248913
0.8557	High Similarity	NPC308726
0.8557	High Similarity	NPC119601
0.8542	High Similarity	NPC88198
0.8511	High Similarity	NPC317586
0.8511	High Similarity	NPC134067
0.8511	High Similarity	NPC470016
0.8469	Intermediate Similarity	NPC33973
0.8469	Intermediate Similarity	NPC70967
0.8454	Intermediate Similarity	NPC163372
0.8454	Intermediate Similarity	NPC302537
0.8454	Intermediate Similarity	NPC469327
0.8404	Intermediate Similarity	NPC169751
0.8404	Intermediate Similarity	NPC240617
0.8404	Intermediate Similarity	NPC272635
0.8404	Intermediate Similarity	NPC166906
0.84	Intermediate Similarity	NPC44063
0.8387	Intermediate Similarity	NPC99380
0.8387	Intermediate Similarity	NPC235704
0.8384	Intermediate Similarity	NPC470251
0.8384	Intermediate Similarity	NPC216245
0.8384	Intermediate Similarity	NPC65523
0.8384	Intermediate Similarity	NPC2436
0.8384	Intermediate Similarity	NPC135854
0.8367	Intermediate Similarity	NPC80781
0.8351	Intermediate Similarity	NPC157787
0.8333	Intermediate Similarity	NPC285513
0.8333	Intermediate Similarity	NPC473036
0.8333	Intermediate Similarity	NPC254496
0.8333	Intermediate Similarity	NPC43747
0.8333	Intermediate Similarity	NPC272898
0.8317	Intermediate Similarity	NPC476479
0.8317	Intermediate Similarity	NPC293850
0.8316	Intermediate Similarity	NPC139570
0.8315	Intermediate Similarity	NPC64600
0.83	Intermediate Similarity	NPC181357
0.8298	Intermediate Similarity	NPC109414
0.8283	Intermediate Similarity	NPC179208
0.8283	Intermediate Similarity	NPC275583
0.8265	Intermediate Similarity	NPC124211
0.8261	Intermediate Similarity	NPC230387
0.8261	Intermediate Similarity	NPC185059
0.8261	Intermediate Similarity	NPC475001
0.8252	Intermediate Similarity	NPC146945
0.8252	Intermediate Similarity	NPC171888
0.8242	Intermediate Similarity	NPC475181
0.8242	Intermediate Similarity	NPC73038
0.8242	Intermediate Similarity	NPC229717
0.8235	Intermediate Similarity	NPC41405
0.8235	Intermediate Similarity	NPC2766
0.8229	Intermediate Similarity	NPC62516
0.8229	Intermediate Similarity	NPC157113
0.8229	Intermediate Similarity	NPC95565
0.8218	Intermediate Similarity	NPC144854
0.8218	Intermediate Similarity	NPC3316
0.8211	Intermediate Similarity	NPC184870
0.82	Intermediate Similarity	NPC213366
0.82	Intermediate Similarity	NPC118911
0.819	Intermediate Similarity	NPC473798
0.8182	Intermediate Similarity	NPC295791
0.8182	Intermediate Similarity	NPC136289
0.8182	Intermediate Similarity	NPC53222
0.8173	Intermediate Similarity	NPC474516
0.8173	Intermediate Similarity	NPC90769
0.8163	Intermediate Similarity	NPC316964
0.8163	Intermediate Similarity	NPC198880
0.8163	Intermediate Similarity	NPC476274
0.8163	Intermediate Similarity	NPC472644
0.8144	Intermediate Similarity	NPC224356
0.8144	Intermediate Similarity	NPC132753
0.8144	Intermediate Similarity	NPC18319
0.8144	Intermediate Similarity	NPC151681
0.8144	Intermediate Similarity	NPC473456
0.8144	Intermediate Similarity	NPC121402
0.8144	Intermediate Similarity	NPC175351
0.8144	Intermediate Similarity	NPC18509
0.8137	Intermediate Similarity	NPC94942
0.8137	Intermediate Similarity	NPC277017
0.8137	Intermediate Similarity	NPC154608
0.8137	Intermediate Similarity	NPC192813
0.8132	Intermediate Similarity	NPC197823
0.8125	Intermediate Similarity	NPC30677
0.8125	Intermediate Similarity	NPC473170
0.8125	Intermediate Similarity	NPC37787
0.8125	Intermediate Similarity	NPC180557
0.8125	Intermediate Similarity	NPC473415
0.8125	Intermediate Similarity	NPC469329
0.8125	Intermediate Similarity	NPC255809
0.8119	Intermediate Similarity	NPC472645
0.8119	Intermediate Similarity	NPC1679
0.8113	Intermediate Similarity	NPC40632
0.8113	Intermediate Similarity	NPC134869
0.8113	Intermediate Similarity	NPC328374
0.8113	Intermediate Similarity	NPC235539
0.8113	Intermediate Similarity	NPC251236
0.8113	Intermediate Similarity	NPC152199
0.8113	Intermediate Similarity	NPC96312
0.8105	Intermediate Similarity	NPC271652
0.8105	Intermediate Similarity	NPC79117
0.8105	Intermediate Similarity	NPC214756
0.8105	Intermediate Similarity	NPC295643
0.8105	Intermediate Similarity	NPC272075
0.81	Intermediate Similarity	NPC90177
0.81	Intermediate Similarity	NPC264048
0.81	Intermediate Similarity	NPC251017
0.8095	Intermediate Similarity	NPC194100
0.8095	Intermediate Similarity	NPC208998
0.8095	Intermediate Similarity	NPC7921
0.8095	Intermediate Similarity	NPC49451
0.809	Intermediate Similarity	NPC473420
0.8085	Intermediate Similarity	NPC20388
0.8085	Intermediate Similarity	NPC128672
0.8085	Intermediate Similarity	NPC134321
0.8081	Intermediate Similarity	NPC476223
0.8081	Intermediate Similarity	NPC81530
0.8081	Intermediate Similarity	NPC115862
0.8081	Intermediate Similarity	NPC472643
0.8081	Intermediate Similarity	NPC476240
0.8081	Intermediate Similarity	NPC224720
0.8081	Intermediate Similarity	NPC118964
0.8077	Intermediate Similarity	NPC43775
0.8077	Intermediate Similarity	NPC201992
0.8065	Intermediate Similarity	NPC473229
0.8061	Intermediate Similarity	NPC260149
0.8061	Intermediate Similarity	NPC58942
0.8061	Intermediate Similarity	NPC478056
0.8058	Intermediate Similarity	NPC286174
0.8058	Intermediate Similarity	NPC77947
0.8043	Intermediate Similarity	NPC6979
0.8043	Intermediate Similarity	NPC325594
0.8043	Intermediate Similarity	NPC473226
0.8043	Intermediate Similarity	NPC56588
0.8041	Intermediate Similarity	NPC476318
0.8041	Intermediate Similarity	NPC154526
0.8041	Intermediate Similarity	NPC98874
0.8041	Intermediate Similarity	NPC471777
0.8041	Intermediate Similarity	NPC471822
0.8041	Intermediate Similarity	NPC476327
0.8041	Intermediate Similarity	NPC7124
0.8041	Intermediate Similarity	NPC328371
0.8041	Intermediate Similarity	NPC219353
0.8041	Intermediate Similarity	NPC327179
0.8041	Intermediate Similarity	NPC472362
0.8041	Intermediate Similarity	NPC472363
0.8039	Intermediate Similarity	NPC475294
0.8039	Intermediate Similarity	NPC9457
0.8039	Intermediate Similarity	NPC471783
0.8022	Intermediate Similarity	NPC120158
0.8022	Intermediate Similarity	NPC475193
0.8021	Intermediate Similarity	NPC191412
0.8021	Intermediate Similarity	NPC114159
0.8021	Intermediate Similarity	NPC6818
0.8021	Intermediate Similarity	NPC74751
0.8021	Intermediate Similarity	NPC103527
0.8021	Intermediate Similarity	NPC293086
0.802	Intermediate Similarity	NPC284865
0.802	Intermediate Similarity	NPC28656
0.802	Intermediate Similarity	NPC235889
0.802	Intermediate Similarity	NPC96268
0.8019	Intermediate Similarity	NPC18547
0.8019	Intermediate Similarity	NPC474906
0.8	Intermediate Similarity	NPC71348
0.8	Intermediate Similarity	NPC472978
0.8	Intermediate Similarity	NPC4036
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC73457
0.8	Intermediate Similarity	NPC185936
0.8	Intermediate Similarity	NPC165250
0.8	Intermediate Similarity	NPC56498
0.8	Intermediate Similarity	NPC289312
0.8	Intermediate Similarity	NPC234042
0.8	Intermediate Similarity	NPC158030
0.8	Intermediate Similarity	NPC168027
0.8	Intermediate Similarity	NPC152117
0.8	Intermediate Similarity	NPC233455
0.8	Intermediate Similarity	NPC11252
0.8	Intermediate Similarity	NPC65120
0.8	Intermediate Similarity	NPC474525
0.8	Intermediate Similarity	NPC22388
0.8	Intermediate Similarity	NPC145067
0.7981	Intermediate Similarity	NPC5284
0.7981	Intermediate Similarity	NPC129689
0.7981	Intermediate Similarity	NPC210005
0.798	Intermediate Similarity	NPC144956
0.798	Intermediate Similarity	NPC205899
0.798	Intermediate Similarity	NPC293890
0.798	Intermediate Similarity	NPC327431
0.798	Intermediate Similarity	NPC46761
0.7979	Intermediate Similarity	NPC77263
0.7979	Intermediate Similarity	NPC250592
0.7963	Intermediate Similarity	NPC297179

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 NPC477435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1978
0.2-0.3	3692
0.3-0.4	2085
0.4-0.5	717
0.5-0.6	238
0.6-0.7	144
0.7-0.8	83
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8673	High Similarity	NPD7128	Approved
0.8673	High Similarity	NPD6675	Approved
0.8673	High Similarity	NPD6402	Approved
0.8673	High Similarity	NPD5739	Approved
0.85	High Similarity	NPD7320	Approved
0.85	High Similarity	NPD6899	Approved
0.85	High Similarity	NPD6881	Approved
0.8416	Intermediate Similarity	NPD6373	Approved
0.8416	Intermediate Similarity	NPD6372	Approved
0.84	Intermediate Similarity	NPD5697	Approved
0.84	Intermediate Similarity	NPD5701	Approved
0.8333	Intermediate Similarity	NPD7290	Approved
0.8333	Intermediate Similarity	NPD6883	Approved
0.8333	Intermediate Similarity	NPD7102	Approved
0.8252	Intermediate Similarity	NPD6617	Approved
0.8252	Intermediate Similarity	NPD6869	Approved
0.8252	Intermediate Similarity	NPD8130	Phase 1
0.8252	Intermediate Similarity	NPD6649	Approved
0.8252	Intermediate Similarity	NPD6650	Approved
0.8252	Intermediate Similarity	NPD6847	Approved
0.8235	Intermediate Similarity	NPD6013	Approved
0.8235	Intermediate Similarity	NPD6012	Approved
0.8235	Intermediate Similarity	NPD6014	Approved
0.8173	Intermediate Similarity	NPD6882	Approved
0.8173	Intermediate Similarity	NPD8297	Approved
0.8144	Intermediate Similarity	NPD4755	Approved
0.8137	Intermediate Similarity	NPD6011	Approved
0.8077	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD7748	Approved
0.8	Intermediate Similarity	NPD7515	Phase 2
0.798	Intermediate Similarity	NPD4696	Approved
0.798	Intermediate Similarity	NPD5286	Approved
0.798	Intermediate Similarity	NPD4700	Approved
0.798	Intermediate Similarity	NPD5285	Approved
0.7959	Intermediate Similarity	NPD6084	Phase 2
0.7959	Intermediate Similarity	NPD7902	Approved
0.7959	Intermediate Similarity	NPD6083	Phase 2
0.7822	Intermediate Similarity	NPD5224	Approved
0.7822	Intermediate Similarity	NPD4633	Approved
0.7822	Intermediate Similarity	NPD5226	Approved
0.7822	Intermediate Similarity	NPD5211	Phase 2
0.7822	Intermediate Similarity	NPD5225	Approved
0.7789	Intermediate Similarity	NPD5328	Approved
0.7778	Intermediate Similarity	NPD6274	Approved
0.7755	Intermediate Similarity	NPD5695	Phase 3
0.7745	Intermediate Similarity	NPD5174	Approved
0.7745	Intermediate Similarity	NPD5175	Approved
0.7732	Intermediate Similarity	NPD6399	Phase 3
0.7727	Intermediate Similarity	NPD7100	Approved
0.7727	Intermediate Similarity	NPD7101	Approved
0.7723	Intermediate Similarity	NPD5223	Approved
0.7677	Intermediate Similarity	NPD4697	Phase 3
0.7677	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5221	Approved
0.7677	Intermediate Similarity	NPD5222	Approved
0.767	Intermediate Similarity	NPD5141	Approved
0.7653	Intermediate Similarity	NPD7900	Approved
0.7653	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6335	Approved
0.7629	Intermediate Similarity	NPD6079	Approved
0.7629	Intermediate Similarity	NPD6411	Approved
0.76	Intermediate Similarity	NPD5173	Approved
0.7596	Intermediate Similarity	NPD4767	Approved
0.7596	Intermediate Similarity	NPD4768	Approved
0.7593	Intermediate Similarity	NPD4632	Approved
0.7589	Intermediate Similarity	NPD6908	Approved
0.7589	Intermediate Similarity	NPD6909	Approved
0.7579	Intermediate Similarity	NPD3573	Approved
0.7573	Intermediate Similarity	NPD4754	Approved
0.7545	Intermediate Similarity	NPD6317	Approved
0.7525	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.7477	Intermediate Similarity	NPD6314	Approved
0.7477	Intermediate Similarity	NPD6313	Approved
0.7474	Intermediate Similarity	NPD3618	Phase 1
0.7455	Intermediate Similarity	NPD6868	Approved
0.7453	Intermediate Similarity	NPD5128	Approved
0.7453	Intermediate Similarity	NPD4730	Approved
0.7453	Intermediate Similarity	NPD4729	Approved
0.7429	Intermediate Similarity	NPD6008	Approved
0.7423	Intermediate Similarity	NPD6101	Approved
0.7423	Intermediate Similarity	NPD4753	Phase 2
0.7423	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7492	Approved
0.7387	Intermediate Similarity	NPD6009	Approved
0.7387	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4202	Approved
0.7345	Intermediate Similarity	NPD6054	Approved
0.7345	Intermediate Similarity	NPD6059	Approved
0.7328	Intermediate Similarity	NPD6616	Approved
0.7315	Intermediate Similarity	NPD4634	Approved
0.7315	Intermediate Similarity	NPD5247	Approved
0.7315	Intermediate Similarity	NPD5248	Approved
0.7315	Intermediate Similarity	NPD5249	Phase 3
0.7315	Intermediate Similarity	NPD5251	Approved
0.7315	Intermediate Similarity	NPD5250	Approved
0.7304	Intermediate Similarity	NPD7604	Phase 2
0.7304	Intermediate Similarity	NPD8328	Phase 3
0.7292	Intermediate Similarity	NPD6684	Approved
0.7292	Intermediate Similarity	NPD7146	Approved
0.7292	Intermediate Similarity	NPD6409	Approved
0.7292	Intermediate Similarity	NPD5330	Approved
0.7292	Intermediate Similarity	NPD7334	Approved
0.7292	Intermediate Similarity	NPD7521	Approved
0.729	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5983	Phase 2
0.7281	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7078	Approved
0.7265	Intermediate Similarity	NPD8293	Discontinued
0.7263	Intermediate Similarity	NPD4786	Approved
0.7248	Intermediate Similarity	NPD5216	Approved
0.7248	Intermediate Similarity	NPD5215	Approved
0.7248	Intermediate Similarity	NPD5217	Approved
0.7245	Intermediate Similarity	NPD6673	Approved
0.7245	Intermediate Similarity	NPD6080	Approved
0.7245	Intermediate Similarity	NPD6904	Approved
0.7234	Intermediate Similarity	NPD3667	Approved
0.7232	Intermediate Similarity	NPD7115	Discovery
0.7222	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6370	Approved
0.7204	Intermediate Similarity	NPD4695	Discontinued
0.7203	Intermediate Similarity	NPD7736	Approved
0.72	Intermediate Similarity	NPD5779	Approved
0.72	Intermediate Similarity	NPD5778	Approved
0.7184	Intermediate Similarity	NPD7638	Approved
0.7179	Intermediate Similarity	NPD6336	Discontinued
0.7174	Intermediate Similarity	NPD3617	Approved
0.7156	Intermediate Similarity	NPD5135	Approved
0.7156	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5169	Approved
0.7156	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6016	Approved
0.713	Intermediate Similarity	NPD6015	Approved
0.7115	Intermediate Similarity	NPD7640	Approved
0.7115	Intermediate Similarity	NPD7639	Approved
0.7113	Intermediate Similarity	NPD5279	Phase 3
0.71	Intermediate Similarity	NPD6050	Approved
0.71	Intermediate Similarity	NPD8035	Phase 2
0.71	Intermediate Similarity	NPD8034	Phase 2
0.7091	Intermediate Similarity	NPD5127	Approved
0.7083	Intermediate Similarity	NPD3665	Phase 1
0.7083	Intermediate Similarity	NPD3133	Approved
0.7083	Intermediate Similarity	NPD3666	Approved
0.7069	Intermediate Similarity	NPD5988	Approved
0.7059	Intermediate Similarity	NPD5210	Approved
0.7059	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4629	Approved
0.7021	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4225	Approved
0.701	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5329	Approved
0.701	Intermediate Similarity	NPD1694	Approved
0.7	Intermediate Similarity	NPD5692	Phase 3
0.6981	Remote Similarity	NPD7632	Discontinued
0.6977	Remote Similarity	NPD7341	Phase 2
0.6972	Remote Similarity	NPD5168	Approved
0.6939	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6098	Approved
0.6931	Remote Similarity	NPD5281	Approved
0.6931	Remote Similarity	NPD5693	Phase 1
0.6931	Remote Similarity	NPD5694	Approved
0.6931	Remote Similarity	NPD5284	Approved
0.6907	Remote Similarity	NPD4197	Approved
0.6903	Remote Similarity	NPD5167	Approved
0.6893	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6116	Phase 1
0.6881	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6412	Phase 2
0.6875	Remote Similarity	NPD6053	Discontinued
0.6875	Remote Similarity	NPD6435	Approved
0.6837	Remote Similarity	NPD1696	Phase 3
0.6796	Remote Similarity	NPD5282	Discontinued
0.6777	Remote Similarity	NPD6033	Approved
0.6774	Remote Similarity	NPD6117	Approved
0.6768	Remote Similarity	NPD4694	Approved
0.6768	Remote Similarity	NPD5280	Approved
0.6768	Remote Similarity	NPD5690	Phase 2
0.675	Remote Similarity	NPD7507	Approved
0.6737	Remote Similarity	NPD7645	Phase 2
0.6735	Remote Similarity	NPD3668	Phase 3
0.6731	Remote Similarity	NPD5654	Approved
0.6701	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4221	Approved
0.6701	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD5368	Approved
0.6635	Remote Similarity	NPD6001	Approved
0.6634	Remote Similarity	NPD5208	Approved
0.6632	Remote Similarity	NPD6114	Approved
0.6632	Remote Similarity	NPD6115	Approved
0.6632	Remote Similarity	NPD6697	Approved
0.6632	Remote Similarity	NPD6118	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