NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	990.5
Volume:	949.634
LogP:	1.459
LogD:	0.985
LogS:	-3.47
# Rotatable Bonds:	11
TPSA:	344.67
# H-Bond Aceptor:	21
# H-Bond Donor:	13
# Rings:	8
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.06
Synthetic Accessibility Score:	6.616
Fsp3:	0.938
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.41
MDCK Permeability:	0.00023254209372680634
Pgp-inhibitor:	0.443
Pgp-substrate:	0.815
Human Intestinal Absorption (HIA):	0.986
20% Bioavailability (F20%):	0.26
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	50.67156219482422%
Volume Distribution (VD):	0.256
Pgp-substrate:	31.091991424560547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	0.666
Half-life (T1/2):	0.762

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.14
Skin Sensitization:	0.042
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC478066

Natural Product ID:	NPC478066
*Common Name:**	methyl (2S,3S,4S,5R,6R)-6-[[(3S,6aR,6bS,7R,8S,8aS,9R,10R,12aS,14aR,14bR)-7,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
IUPAC Name:	methyl (2S,3S,4S,5R,6R)-6-[[(3S,6aR,6bS,7R,8S,8aS,9R,10R,12aS,14aR,14bR)-7,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
Synonyms:
Standard InCHIKey:	HAKHPDLODDSOTK-XWMBHQINSA-N
Standard InCHI:	InChI=1S/C48H78O21/c1-43(2)15-20-19-9-10-24-45(5)13-12-25(44(3,4)23(45)11-14-46(24,6)47(19,7)36(59)38(61)48(20,18-51)37(60)35(43)58)66-42-33(68-41-30(56)28(54)26(52)21(16-49)64-41)31(57)32(34(69-42)39(62)63-8)67-40-29(55)27(53)22(17-50)65-40/h9,20-38,40-42,49-61H,10-18H2,1-8H3/t20-,21+,22-,23?,24+,25-,26+,27-,28-,29+,30+,31-,32-,33+,34-,35-,36-,37-,38+,40-,41-,42+,45-,46+,47-,48+/m0/s1
SMILES:	C[C@]12CC[C@@H](C(C1CC[C@@]3([C@@H]2CC=C4[C@]3([C@H]([C@H]([C@@]5([C@H]4CC([C@H]([C@@H]5O)O)(C)C)CO)O)O)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)OC)O[C@H]7[C@@H]([C@H]([C@@H](O7)CO)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44575722
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	n.a.	n.a.	PMID[15620235]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	Nanning City, Guangxi Province, People's Republic of China	1997-Jan	PMID[17190442]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8121	Symplocos chinensis	Species	Symplocaceae	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	4
Others	1

Activity Type	# Activity
Cell Line	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.3	ug/ml	PMID[15620235]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	6.8	ug/ml	PMID[15620235]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.66	ug/ml	PMID[15620235]
NPT27	Others	Unspecified		IC50	>	10	ug/ml	PMID[15620235]
NPT2	Others	Unspecified		Ratio IC50	=	33	n.a.	PMID[15620235]

☑ 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 NPC478066 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	294
0.1-0.2	1812
0.2-0.3	5386
0.3-0.4	10737
0.4-0.5	10465
0.5-0.6	6927
0.6-0.7	4006
0.7-0.8	1923
0.8-0.85	483
0.85-0.9	422
0.9-0.95	208
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC470477
0.9737	High Similarity	NPC235438
0.9737	High Similarity	NPC107966
0.9737	High Similarity	NPC249848
0.9737	High Similarity	NPC40775
0.9652	High Similarity	NPC30735
0.9652	High Similarity	NPC281148
0.9652	High Similarity	NPC235405
0.9569	High Similarity	NPC23275
0.9565	High Similarity	NPC213952
0.9561	High Similarity	NPC118440
0.9561	High Similarity	NPC236657
0.9496	High Similarity	NPC262796
0.9496	High Similarity	NPC264566
0.9496	High Similarity	NPC475167
0.9496	High Similarity	NPC478065
0.9496	High Similarity	NPC329993
0.9496	High Similarity	NPC478064
0.9496	High Similarity	NPC172374
0.9496	High Similarity	NPC475377
0.9496	High Similarity	NPC476074
0.9496	High Similarity	NPC45346
0.9496	High Similarity	NPC134914
0.9496	High Similarity	NPC173435
0.9496	High Similarity	NPC301639
0.9487	High Similarity	NPC285091
0.9487	High Similarity	NPC470218
0.9483	High Similarity	NPC257211
0.9478	High Similarity	NPC159309
0.9478	High Similarity	NPC64715
0.9478	High Similarity	NPC222580
0.9478	High Similarity	NPC86222
0.9478	High Similarity	NPC62725
0.9478	High Similarity	NPC297263
0.9478	High Similarity	NPC11242
0.9478	High Similarity	NPC171544
0.9478	High Similarity	NPC104372
0.9478	High Similarity	NPC223301
0.9478	High Similarity	NPC75417
0.9478	High Similarity	NPC22956
0.9478	High Similarity	NPC114484
0.9478	High Similarity	NPC301449
0.9478	High Similarity	NPC31838
0.9478	High Similarity	NPC187618
0.9478	High Similarity	NPC302887
0.9474	High Similarity	NPC180550
0.9474	High Similarity	NPC472949
0.9474	High Similarity	NPC309780
0.9474	High Similarity	NPC208381
0.9474	High Similarity	NPC473884
0.9474	High Similarity	NPC469945
0.9474	High Similarity	NPC475171
0.9474	High Similarity	NPC114441
0.9474	High Similarity	NPC157868
0.9474	High Similarity	NPC35405
0.9474	High Similarity	NPC6377
0.9474	High Similarity	NPC214484
0.9474	High Similarity	NPC11551
0.9474	High Similarity	NPC39211
0.9469	High Similarity	NPC224121
0.9417	High Similarity	NPC478153
0.9417	High Similarity	NPC478150
0.9417	High Similarity	NPC478152
0.9402	High Similarity	NPC33068
0.9397	High Similarity	NPC4749
0.9397	High Similarity	NPC80986
0.9397	High Similarity	NPC10607
0.9397	High Similarity	NPC187290
0.9397	High Similarity	NPC236870
0.9397	High Similarity	NPC131469
0.9397	High Similarity	NPC162574
0.9397	High Similarity	NPC475591
0.9397	High Similarity	NPC21691
0.9397	High Similarity	NPC313110
0.9386	High Similarity	NPC286347
0.9339	High Similarity	NPC478151
0.9333	High Similarity	NPC25998
0.9333	High Similarity	NPC478155
0.9328	High Similarity	NPC475281
0.9328	High Similarity	NPC477075
0.9328	High Similarity	NPC477078
0.9328	High Similarity	NPC329923
0.9322	High Similarity	NPC181066
0.9322	High Similarity	NPC284449
0.9322	High Similarity	NPC469947
0.9316	High Similarity	NPC471964
0.9316	High Similarity	NPC200049
0.9316	High Similarity	NPC258617
0.9316	High Similarity	NPC262199
0.9316	High Similarity	NPC471961
0.9316	High Similarity	NPC202666
0.9316	High Similarity	NPC44716
0.9316	High Similarity	NPC14617
0.9316	High Similarity	NPC2370
0.9316	High Similarity	NPC283417
0.9316	High Similarity	NPC302543
0.931	High Similarity	NPC31193
0.931	High Similarity	NPC242840
0.9304	High Similarity	NPC192791
0.9256	High Similarity	NPC478154
0.925	High Similarity	NPC470913
0.925	High Similarity	NPC477077
0.925	High Similarity	NPC477076
0.925	High Similarity	NPC470912
0.925	High Similarity	NPC477079
0.9237	High Similarity	NPC471962
0.9237	High Similarity	NPC247315
0.9237	High Similarity	NPC471963
0.9237	High Similarity	NPC160452
0.9231	High Similarity	NPC471965
0.9224	High Similarity	NPC473645
0.9224	High Similarity	NPC294112
0.9217	High Similarity	NPC232237
0.9217	High Similarity	NPC105800
0.9174	High Similarity	NPC477197
0.9167	High Similarity	NPC477194
0.9167	High Similarity	NPC477193
0.9167	High Similarity	NPC477192
0.9167	High Similarity	NPC477191
0.916	High Similarity	NPC475368
0.9138	High Similarity	NPC207738
0.913	High Similarity	NPC300419
0.9123	High Similarity	NPC475633
0.9098	High Similarity	NPC277212
0.9098	High Similarity	NPC178264
0.9098	High Similarity	NPC192765
0.9098	High Similarity	NPC46823
0.9098	High Similarity	NPC30279
0.9098	High Similarity	NPC473918
0.9098	High Similarity	NPC71391
0.9091	High Similarity	NPC141600
0.9091	High Similarity	NPC88311
0.9091	High Similarity	NPC11577
0.9091	High Similarity	NPC269484
0.9091	High Similarity	NPC252289
0.9091	High Similarity	NPC9470
0.9091	High Similarity	NPC477196
0.9091	High Similarity	NPC115656
0.9091	High Similarity	NPC472267
0.9091	High Similarity	NPC305793
0.9091	High Similarity	NPC97918
0.9091	High Similarity	NPC280029
0.9091	High Similarity	NPC470518
0.9091	High Similarity	NPC1314
0.9091	High Similarity	NPC82380
0.9091	High Similarity	NPC252657
0.9091	High Similarity	NPC107536
0.9091	High Similarity	NPC273878
0.9091	High Similarity	NPC244296
0.9076	High Similarity	NPC130229
0.9068	High Similarity	NPC275343
0.906	High Similarity	NPC37860
0.906	High Similarity	NPC267694
0.906	High Similarity	NPC153673
0.906	High Similarity	NPC142151
0.906	High Similarity	NPC110385
0.906	High Similarity	NPC144644
0.9052	High Similarity	NPC109588
0.9043	High Similarity	NPC291903
0.9043	High Similarity	NPC37134
0.9035	High Similarity	NPC475208
0.9035	High Similarity	NPC238935
0.9024	High Similarity	NPC225791
0.9016	High Similarity	NPC476775
0.9016	High Similarity	NPC271610
0.9016	High Similarity	NPC476774
0.9016	High Similarity	NPC476780
0.9008	High Similarity	NPC470475
0.8983	High Similarity	NPC68767
0.8983	High Similarity	NPC51099
0.8983	High Similarity	NPC293031
0.8983	High Similarity	NPC275225
0.8966	High Similarity	NPC473824
0.8966	High Similarity	NPC475119
0.8957	High Similarity	NPC475486
0.8957	High Similarity	NPC164389
0.8947	High Similarity	NPC80843
0.8947	High Similarity	NPC48249
0.8947	High Similarity	NPC256798
0.8947	High Similarity	NPC1046
0.8947	High Similarity	NPC128925
0.8947	High Similarity	NPC116794
0.8947	High Similarity	NPC473383
0.8947	High Similarity	NPC139894
0.8943	High Similarity	NPC476776
0.8943	High Similarity	NPC477195
0.8943	High Similarity	NPC312650
0.8934	High Similarity	NPC265841
0.8934	High Similarity	NPC47995
0.8926	High Similarity	NPC470780
0.8889	High Similarity	NPC475899
0.8889	High Similarity	NPC237191
0.8879	High Similarity	NPC471384
0.8879	High Similarity	NPC160415
0.8879	High Similarity	NPC75287
0.8879	High Similarity	NPC161674
0.8879	High Similarity	NPC51465
0.8879	High Similarity	NPC305267
0.8879	High Similarity	NPC58448
0.8879	High Similarity	NPC288205

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 NPC478066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	2062
0.2-0.3	4027
0.3-0.4	1812
0.4-0.5	534
0.5-0.6	289
0.6-0.7	132
0.7-0.8	43
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9316	High Similarity	NPD8328	Phase 3
0.9298	High Similarity	NPD8295	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7736	Approved
0.792	Intermediate Similarity	NPD8517	Approved
0.792	Intermediate Similarity	NPD8513	Phase 3
0.792	Intermediate Similarity	NPD8516	Approved
0.792	Intermediate Similarity	NPD8515	Approved
0.7891	Intermediate Similarity	NPD8293	Discontinued
0.7787	Intermediate Similarity	NPD8133	Approved
0.7717	Intermediate Similarity	NPD6370	Approved
0.7634	Intermediate Similarity	NPD7319	Approved
0.7597	Intermediate Similarity	NPD7492	Approved
0.7559	Intermediate Similarity	NPD6054	Approved
0.7559	Intermediate Similarity	NPD6059	Approved
0.7538	Intermediate Similarity	NPD7507	Approved
0.7538	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD8033	Approved
0.7481	Intermediate Similarity	NPD7078	Approved
0.7438	Intermediate Similarity	NPD6412	Phase 2
0.7422	Intermediate Similarity	NPD6319	Approved
0.7422	Intermediate Similarity	NPD8294	Approved
0.7422	Intermediate Similarity	NPD8377	Approved
0.7377	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6686	Approved
0.7364	Intermediate Similarity	NPD8380	Approved
0.7364	Intermediate Similarity	NPD6016	Approved
0.7364	Intermediate Similarity	NPD8335	Approved
0.7364	Intermediate Similarity	NPD6015	Approved
0.7364	Intermediate Similarity	NPD8379	Approved
0.7364	Intermediate Similarity	NPD8378	Approved
0.7364	Intermediate Similarity	NPD8296	Approved
0.7308	Intermediate Similarity	NPD5988	Approved
0.728	Intermediate Similarity	NPD6882	Approved
0.728	Intermediate Similarity	NPD8297	Approved
0.7209	Intermediate Similarity	NPD7516	Approved
0.7203	Intermediate Similarity	NPD7902	Approved
0.72	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6009	Approved
0.7177	Intermediate Similarity	NPD6372	Approved
0.7177	Intermediate Similarity	NPD6373	Approved
0.7132	Intermediate Similarity	NPD7327	Approved
0.7132	Intermediate Similarity	NPD7328	Approved
0.7131	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7748	Approved
0.709	Intermediate Similarity	NPD8074	Phase 3
0.7073	Intermediate Similarity	NPD7128	Approved
0.7073	Intermediate Similarity	NPD6675	Approved
0.7073	Intermediate Similarity	NPD5739	Approved
0.7073	Intermediate Similarity	NPD6402	Approved
0.7063	Intermediate Similarity	NPD6650	Approved
0.7063	Intermediate Similarity	NPD6649	Approved
0.7037	Intermediate Similarity	NPD6033	Approved
0.697	Remote Similarity	NPD7503	Approved
0.696	Remote Similarity	NPD6881	Approved
0.696	Remote Similarity	NPD7320	Approved
0.696	Remote Similarity	NPD6899	Approved
0.6953	Remote Similarity	NPD4632	Approved
0.6949	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7900	Approved
0.6929	Remote Similarity	NPD8130	Phase 1
0.6923	Remote Similarity	NPD7515	Phase 2
0.688	Remote Similarity	NPD5697	Approved
0.688	Remote Similarity	NPD5701	Approved
0.686	Remote Similarity	NPD4225	Approved
0.685	Remote Similarity	NPD6883	Approved
0.685	Remote Similarity	NPD7290	Approved
0.685	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6921	Approved
0.6797	Remote Similarity	NPD6617	Approved
0.6797	Remote Similarity	NPD6869	Approved
0.6797	Remote Similarity	NPD6847	Approved
0.6794	Remote Similarity	NPD7115	Discovery
0.678	Remote Similarity	NPD8035	Phase 2
0.678	Remote Similarity	NPD8034	Phase 2
0.678	Remote Similarity	NPD6411	Approved
0.6772	Remote Similarity	NPD6014	Approved
0.6772	Remote Similarity	NPD6013	Approved
0.6772	Remote Similarity	NPD6012	Approved
0.6741	Remote Similarity	NPD7604	Phase 2
0.6723	Remote Similarity	NPD6399	Phase 3
0.6721	Remote Similarity	NPD7638	Approved
0.6719	Remote Similarity	NPD4634	Approved
0.6716	Remote Similarity	NPD5983	Phase 2
0.6693	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7640	Approved
0.6642	Remote Similarity	NPD6336	Discontinued
0.6641	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6067	Discontinued
0.661	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6101	Approved
0.6593	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8171	Discontinued
0.6544	Remote Similarity	NPD8080	Discontinued
0.6504	Remote Similarity	NPD6083	Phase 2
0.6504	Remote Similarity	NPD6084	Phase 2
0.6504	Remote Similarity	NPD4755	Approved
0.65	Remote Similarity	NPD7983	Approved
0.6466	Remote Similarity	NPD6274	Approved
0.646	Remote Similarity	NPD7645	Phase 2
0.6446	Remote Similarity	NPD5778	Approved
0.6446	Remote Similarity	NPD5779	Approved
0.6444	Remote Similarity	NPD7101	Approved
0.6444	Remote Similarity	NPD7100	Approved
0.6434	Remote Similarity	NPD8450	Suspended
0.6423	Remote Similarity	NPD4697	Phase 3
0.6418	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5286	Approved
0.64	Remote Similarity	NPD5285	Approved
0.64	Remote Similarity	NPD4696	Approved
0.64	Remote Similarity	NPD4700	Approved
0.637	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD8449	Approved
0.6364	Remote Similarity	NPD7799	Discontinued
0.6357	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8448	Approved
0.6357	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6908	Approved
0.635	Remote Similarity	NPD6909	Approved
0.6345	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6868	Approved
0.6338	Remote Similarity	NPD5956	Approved
0.6333	Remote Similarity	NPD5328	Approved
0.6331	Remote Similarity	NPD8341	Approved
0.6331	Remote Similarity	NPD8299	Approved
0.6331	Remote Similarity	NPD8342	Approved
0.6331	Remote Similarity	NPD8340	Approved
0.632	Remote Similarity	NPD5696	Approved
0.6301	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5224	Approved
0.6299	Remote Similarity	NPD5225	Approved
0.6299	Remote Similarity	NPD5211	Phase 2
0.6299	Remote Similarity	NPD5226	Approved
0.6299	Remote Similarity	NPD4633	Approved
0.6296	Remote Similarity	NPD6317	Approved
0.629	Remote Similarity	NPD5221	Approved
0.629	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.629	Remote Similarity	NPD5222	Approved
0.6286	Remote Similarity	NPD8451	Approved
0.6279	Remote Similarity	NPD4767	Approved
0.6279	Remote Similarity	NPD4768	Approved
0.6276	Remote Similarity	NPD8415	Approved
0.626	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD6672	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD6313	Approved
0.625	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD6314	Approved
0.625	Remote Similarity	NPD5175	Approved
0.624	Remote Similarity	NPD5173	Approved
0.6232	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6079	Approved
0.6224	Remote Similarity	NPD8392	Approved
0.6224	Remote Similarity	NPD8391	Approved
0.6224	Remote Similarity	NPD8390	Approved
0.622	Remote Similarity	NPD5223	Approved
0.6218	Remote Similarity	NPD3618	Phase 1
0.621	Remote Similarity	NPD5695	Phase 3
0.6202	Remote Similarity	NPD5141	Approved
0.6198	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD8336	Approved
0.6197	Remote Similarity	NPD8337	Approved
0.619	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4786	Approved
0.6183	Remote Similarity	NPD4730	Approved
0.6183	Remote Similarity	NPD4729	Approved
0.6181	Remote Similarity	NPD7260	Phase 2
0.6174	Remote Similarity	NPD7329	Approved
0.6172	Remote Similarity	NPD7632	Discontinued
0.6167	Remote Similarity	NPD3573	Approved
0.616	Remote Similarity	NPD7839	Suspended
0.6154	Remote Similarity	NPD3667	Approved
0.6148	Remote Similarity	NPD6698	Approved
0.6148	Remote Similarity	NPD46	Approved
0.6144	Remote Similarity	NPD7625	Phase 1
0.6143	Remote Similarity	NPD7829	Approved
0.6143	Remote Similarity	NPD7830	Approved
0.6138	Remote Similarity	NPD8338	Approved
0.6124	Remote Similarity	NPD4754	Approved
0.6116	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD8444	Approved
0.6105	Remote Similarity	NPD8407	Phase 2
0.6102	Remote Similarity	NPD3669	Approved
0.6102	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7637	Suspended
0.6094	Remote Similarity	NPD1700	Approved
0.609	Remote Similarity	NPD5249	Phase 3
0.609	Remote Similarity	NPD5250	Approved
0.609	Remote Similarity	NPD5251	Approved
0.609	Remote Similarity	NPD5248	Approved
0.609	Remote Similarity	NPD5247	Approved
0.6061	Remote Similarity	NPD5128	Approved
0.604	Remote Similarity	NPD6333	Approved
0.604	Remote Similarity	NPD6334	Approved
0.6027	Remote Similarity	NPD6845	Suspended

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