NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	620.27
Volume:	595.562
LogP:	4.226
LogD:	2.304
LogS:	-5.766
# Rotatable Bonds:	11
TPSA:	159.16
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.186
Synthetic Accessibility Score:	5.392
Fsp3:	0.966
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:	-4.835
MDCK Permeability:	3.505409404169768e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.118

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	94.89456939697266%
Volume Distribution (VD):	1.38
Pgp-substrate:	2.31770396232605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.192
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	1.778
Half-life (T1/2):	0.005

ADMET: Toxicity

hERG Blockers:	0.975
Human Hepatotoxicity (H-HT):	0.696
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.966
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.852
Skin Sensitization:	0.986
Carcinogencity:	0.804
Eye Corrosion:	0.984
Eye Irritation:	0.379
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC478104

Natural Product ID:	NPC478104
*Common Name:**	disodium;[(3S,6S,10S,13S,17R)-17-[(2S,3R)-3-acetyloxy-6-methylheptan-2-yl]-10,13-dimethyl-3-sulfonatooxy-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl] sulfate
IUPAC Name:	disodium;[(3S,6S,10S,13S,17R)-17-[(2S,3R)-3-acetyloxy-6-methylheptan-2-yl]-10,13-dimethyl-3-sulfonatooxy-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl] sulfate
Synonyms:
Standard InCHIKey:	YWONMSRPQMZJCK-YXGYXVMJSA-L
Standard InCHI:	InChI=1S/C29H48O10S2.2Na/c1-17(2)7-10-26(37-19(4)30)18(3)22-8-9-23-21-16-27(39-41(34,35)36)25-15-20(38-40(31,32)33)11-13-29(25,6)24(21)12-14-28(22,23)5;;/h12,17-18,20-23,25-27H,7-11,13-16H2,1-6H3,(H,31,32,33)(H,34,35,36);;/q;2*+1/p-2/t18-,20-,21?,22+,23?,25?,26+,27-,28+,29+;;/m0../s1
SMILES:	C[C@@H]([C@H]1CCC2[C@@]1(CC=C3C2C[C@@H](C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)[O-])C)OS(=O)(=O)[O-])C)[C@@H](CCC(C)C)OC(=O)C.[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL436059
PubChem CID:	24943516
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids

*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
NPO33662	Tremaster novaecaledonia	Species	Asterinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]

☑ 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
EC50	2
IC50	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	EC50	=	18000	nM	PMID[8145229]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	EC50	=	3000	nM	PMID[8145229]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	150000	nM	PMID[8145229]
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	IC50	>	150000	nM	PMID[8145229]

☑ 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 NPC478104 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	190
0.1-0.2	1525
0.2-0.3	6904
0.3-0.4	16230
0.4-0.5	6598
0.5-0.6	5664
0.6-0.7	4812
0.7-0.8	751
0.8-0.85	15
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.878	High Similarity	NPC153987
0.878	High Similarity	NPC44083
0.8721	High Similarity	NPC474970
0.8706	High Similarity	NPC478102
0.8659	High Similarity	NPC475337
0.8588	High Similarity	NPC139206
0.8571	High Similarity	NPC473534
0.8556	High Similarity	NPC473678
0.8523	High Similarity	NPC470613
0.8523	High Similarity	NPC470612
0.8506	High Similarity	NPC286153
0.8506	High Similarity	NPC478094
0.8452	Intermediate Similarity	NPC269791
0.8333	Intermediate Similarity	NPC471896
0.8293	Intermediate Similarity	NPC478105
0.828	Intermediate Similarity	NPC475178
0.8276	Intermediate Similarity	NPC469878
0.8256	Intermediate Similarity	NPC286786
0.8235	Intermediate Similarity	NPC304194
0.8161	Intermediate Similarity	NPC132386
0.8152	Intermediate Similarity	NPC38232
0.814	Intermediate Similarity	NPC195334
0.814	Intermediate Similarity	NPC290495
0.8132	Intermediate Similarity	NPC148414
0.8132	Intermediate Similarity	NPC175628
0.8132	Intermediate Similarity	NPC111585
0.8118	Intermediate Similarity	NPC305835
0.8118	Intermediate Similarity	NPC47808
0.809	Intermediate Similarity	NPC264127
0.809	Intermediate Similarity	NPC477604
0.8085	Intermediate Similarity	NPC304899
0.8085	Intermediate Similarity	NPC253115
0.8085	Intermediate Similarity	NPC88009
0.8043	Intermediate Similarity	NPC177641
0.8043	Intermediate Similarity	NPC26888
0.8023	Intermediate Similarity	NPC206735
0.8022	Intermediate Similarity	NPC474889
0.8022	Intermediate Similarity	NPC473647
0.8022	Intermediate Similarity	NPC474704
0.8022	Intermediate Similarity	NPC475921
0.8021	Intermediate Similarity	NPC230546
0.8	Intermediate Similarity	NPC475313
0.8	Intermediate Similarity	NPC475033
0.8	Intermediate Similarity	NPC475032
0.8	Intermediate Similarity	NPC474684
0.8	Intermediate Similarity	NPC142361
0.8	Intermediate Similarity	NPC210337
0.7978	Intermediate Similarity	NPC474013
0.7978	Intermediate Similarity	NPC478127
0.7957	Intermediate Similarity	NPC475255
0.7957	Intermediate Similarity	NPC470375
0.7957	Intermediate Similarity	NPC470376
0.7957	Intermediate Similarity	NPC470224
0.7957	Intermediate Similarity	NPC478129
0.7955	Intermediate Similarity	NPC473742
0.7955	Intermediate Similarity	NPC474789
0.7955	Intermediate Similarity	NPC52108
0.7931	Intermediate Similarity	NPC108476
0.7931	Intermediate Similarity	NPC142163
0.7912	Intermediate Similarity	NPC473879
0.7912	Intermediate Similarity	NPC97884
0.7912	Intermediate Similarity	NPC472220
0.7895	Intermediate Similarity	NPC276103
0.7895	Intermediate Similarity	NPC54248
0.7889	Intermediate Similarity	NPC84121
0.7889	Intermediate Similarity	NPC137306
0.7872	Intermediate Similarity	NPC474922
0.7872	Intermediate Similarity	NPC159410
0.7865	Intermediate Similarity	NPC100391
0.7857	Intermediate Similarity	NPC476471
0.7857	Intermediate Similarity	NPC475344
0.7849	Intermediate Similarity	NPC189520
0.7849	Intermediate Similarity	NPC234335
0.7841	Intermediate Similarity	NPC256112
0.7841	Intermediate Similarity	NPC328351
0.7835	Intermediate Similarity	NPC473510
0.7835	Intermediate Similarity	NPC208358
0.7826	Intermediate Similarity	NPC472240
0.7826	Intermediate Similarity	NPC477606
0.7826	Intermediate Similarity	NPC177141
0.7826	Intermediate Similarity	NPC474679
0.7826	Intermediate Similarity	NPC262858
0.7816	Intermediate Similarity	NPC322313
0.7816	Intermediate Similarity	NPC102253
0.7816	Intermediate Similarity	NPC236237
0.7812	Intermediate Similarity	NPC23680
0.7802	Intermediate Similarity	NPC159046
0.7802	Intermediate Similarity	NPC187376
0.7802	Intermediate Similarity	NPC46912
0.7802	Intermediate Similarity	NPC162107
0.7802	Intermediate Similarity	NPC233836
0.7791	Intermediate Similarity	NPC244385
0.7791	Intermediate Similarity	NPC167037
0.7791	Intermediate Similarity	NPC6978
0.7791	Intermediate Similarity	NPC138621
0.7789	Intermediate Similarity	NPC184848
0.7789	Intermediate Similarity	NPC69548
0.7789	Intermediate Similarity	NPC279974
0.7778	Intermediate Similarity	NPC474124
0.7778	Intermediate Similarity	NPC98270
0.7778	Intermediate Similarity	NPC470223
0.7778	Intermediate Similarity	NPC191965
0.7778	Intermediate Similarity	NPC473523
0.7766	Intermediate Similarity	NPC170220
0.7766	Intermediate Similarity	NPC141497
0.7766	Intermediate Similarity	NPC107674
0.7765	Intermediate Similarity	NPC189883
0.7755	Intermediate Similarity	NPC475617
0.7755	Intermediate Similarity	NPC155974
0.7753	Intermediate Similarity	NPC5280
0.7742	Intermediate Similarity	NPC302280
0.7742	Intermediate Similarity	NPC474842
0.7742	Intermediate Similarity	NPC475965
0.7732	Intermediate Similarity	NPC477813
0.7727	Intermediate Similarity	NPC476101
0.7727	Intermediate Similarity	NPC170303
0.7727	Intermediate Similarity	NPC25554
0.7717	Intermediate Similarity	NPC93411
0.7717	Intermediate Similarity	NPC28227
0.7717	Intermediate Similarity	NPC242864
0.7708	Intermediate Similarity	NPC471903
0.7708	Intermediate Similarity	NPC327788
0.7701	Intermediate Similarity	NPC100906
0.7701	Intermediate Similarity	NPC1319
0.7701	Intermediate Similarity	NPC474132
0.7701	Intermediate Similarity	NPC273410
0.7701	Intermediate Similarity	NPC80530
0.77	Intermediate Similarity	NPC473543
0.7692	Intermediate Similarity	NPC329943
0.7692	Intermediate Similarity	NPC91525
0.7692	Intermediate Similarity	NPC73038
0.7692	Intermediate Similarity	NPC10005
0.7692	Intermediate Similarity	NPC168231
0.7692	Intermediate Similarity	NPC325594
0.7692	Intermediate Similarity	NPC9892
0.7692	Intermediate Similarity	NPC195640
0.7692	Intermediate Similarity	NPC55309
0.7692	Intermediate Similarity	NPC28252
0.7692	Intermediate Similarity	NPC155011
0.7677	Intermediate Similarity	NPC22388
0.7674	Intermediate Similarity	NPC214570
0.7667	Intermediate Similarity	NPC239362
0.7667	Intermediate Similarity	NPC299963
0.7667	Intermediate Similarity	NPC318515
0.7667	Intermediate Similarity	NPC124172
0.7667	Intermediate Similarity	NPC25833
0.7667	Intermediate Similarity	NPC475509
0.766	Intermediate Similarity	NPC110657
0.766	Intermediate Similarity	NPC297265
0.766	Intermediate Similarity	NPC212301
0.766	Intermediate Similarity	NPC86266
0.766	Intermediate Similarity	NPC154101
0.766	Intermediate Similarity	NPC23434
0.7647	Intermediate Similarity	NPC141071
0.7647	Intermediate Similarity	NPC471723
0.7647	Intermediate Similarity	NPC257347
0.764	Intermediate Similarity	NPC30166
0.764	Intermediate Similarity	NPC477599
0.764	Intermediate Similarity	NPC471218
0.764	Intermediate Similarity	NPC470049
0.764	Intermediate Similarity	NPC472504
0.7634	Intermediate Similarity	NPC474570
0.7634	Intermediate Similarity	NPC84271
0.7634	Intermediate Similarity	NPC146554
0.7634	Intermediate Similarity	NPC247312
0.7634	Intermediate Similarity	NPC271974
0.7634	Intermediate Similarity	NPC16265
0.7634	Intermediate Similarity	NPC77168
0.7634	Intermediate Similarity	NPC102414
0.7634	Intermediate Similarity	NPC475049
0.7629	Intermediate Similarity	NPC226986
0.7629	Intermediate Similarity	NPC141401
0.7624	Intermediate Similarity	NPC475571
0.7614	Intermediate Similarity	NPC236112
0.7614	Intermediate Similarity	NPC469802
0.7609	Intermediate Similarity	NPC167877
0.7609	Intermediate Similarity	NPC166857
0.7604	Intermediate Similarity	NPC45324
0.7604	Intermediate Similarity	NPC469599
0.7604	Intermediate Similarity	NPC474909
0.7604	Intermediate Similarity	NPC162001
0.7604	Intermediate Similarity	NPC222845
0.7586	Intermediate Similarity	NPC285761
0.7586	Intermediate Similarity	NPC275910
0.7582	Intermediate Similarity	NPC323765
0.7579	Intermediate Similarity	NPC474185
0.7579	Intermediate Similarity	NPC476304
0.7579	Intermediate Similarity	NPC79117
0.7579	Intermediate Similarity	NPC214697
0.7558	Intermediate Similarity	NPC134330
0.7558	Intermediate Similarity	NPC73875
0.7558	Intermediate Similarity	NPC300324
0.7558	Intermediate Similarity	NPC237460
0.7558	Intermediate Similarity	NPC240604
0.7558	Intermediate Similarity	NPC321381
0.7558	Intermediate Similarity	NPC129165
0.7558	Intermediate Similarity	NPC107059
0.7558	Intermediate Similarity	NPC202642
0.7558	Intermediate Similarity	NPC46160
0.7558	Intermediate Similarity	NPC321016

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 NPC478104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1657
0.2-0.3	4533
0.3-0.4	2023
0.4-0.5	367
0.5-0.6	173
0.6-0.7	178
0.7-0.8	65
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7957	Intermediate Similarity	NPD6399	Phase 3
0.7826	Intermediate Similarity	NPD6051	Approved
0.7816	Intermediate Similarity	NPD7525	Registered
0.7717	Intermediate Similarity	NPD6672	Approved
0.7717	Intermediate Similarity	NPD5737	Approved
0.7692	Intermediate Similarity	NPD6684	Approved
0.7692	Intermediate Similarity	NPD7146	Approved
0.7692	Intermediate Similarity	NPD6409	Approved
0.7692	Intermediate Similarity	NPD5330	Approved
0.7692	Intermediate Similarity	NPD7521	Approved
0.7692	Intermediate Similarity	NPD7334	Approved
0.7667	Intermediate Similarity	NPD3668	Phase 3
0.7527	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8034	Phase 2
0.7474	Intermediate Similarity	NPD8035	Phase 2
0.7451	Intermediate Similarity	NPD6402	Approved
0.7451	Intermediate Similarity	NPD6675	Approved
0.7451	Intermediate Similarity	NPD7128	Approved
0.7451	Intermediate Similarity	NPD5739	Approved
0.7442	Intermediate Similarity	NPD7339	Approved
0.7442	Intermediate Similarity	NPD6942	Approved
0.7423	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD6373	Approved
0.7404	Intermediate Similarity	NPD6372	Approved
0.7374	Intermediate Similarity	NPD7638	Approved
0.732	Intermediate Similarity	NPD7748	Approved
0.7312	Intermediate Similarity	NPD6098	Approved
0.7308	Intermediate Similarity	NPD7320	Approved
0.7308	Intermediate Similarity	NPD6881	Approved
0.7308	Intermediate Similarity	NPD6899	Approved
0.73	Intermediate Similarity	NPD7639	Approved
0.73	Intermediate Similarity	NPD7640	Approved
0.7283	Intermediate Similarity	NPD4786	Approved
0.7282	Intermediate Similarity	NPD6008	Approved
0.7273	Intermediate Similarity	NPD7902	Approved
0.7264	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6650	Approved
0.7264	Intermediate Similarity	NPD6649	Approved
0.7263	Intermediate Similarity	NPD5328	Approved
0.7263	Intermediate Similarity	NPD6080	Approved
0.7263	Intermediate Similarity	NPD6904	Approved
0.7263	Intermediate Similarity	NPD6673	Approved
0.7212	Intermediate Similarity	NPD5701	Approved
0.7212	Intermediate Similarity	NPD5697	Approved
0.7204	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6882	Approved
0.7196	Intermediate Similarity	NPD8297	Approved
0.717	Intermediate Similarity	NPD7102	Approved
0.717	Intermediate Similarity	NPD6883	Approved
0.717	Intermediate Similarity	NPD7290	Approved
0.7159	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6011	Approved
0.7128	Intermediate Similarity	NPD3618	Phase 1
0.7113	Intermediate Similarity	NPD6079	Approved
0.7113	Intermediate Similarity	NPD7515	Phase 2
0.7111	Intermediate Similarity	NPD7645	Phase 2
0.7103	Intermediate Similarity	NPD6869	Approved
0.7103	Intermediate Similarity	NPD6847	Approved
0.7103	Intermediate Similarity	NPD6617	Approved
0.7103	Intermediate Similarity	NPD8130	Phase 1
0.71	Intermediate Similarity	NPD6083	Phase 2
0.71	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6014	Approved
0.7075	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD6013	Approved
0.7065	Intermediate Similarity	NPD3667	Approved
0.7041	Intermediate Similarity	NPD4202	Approved
0.6979	Remote Similarity	NPD5208	Approved
0.697	Remote Similarity	NPD6001	Approved
0.6939	Remote Similarity	NPD6050	Approved
0.6939	Remote Similarity	NPD5693	Phase 1
0.6931	Remote Similarity	NPD4755	Approved
0.69	Remote Similarity	NPD5695	Phase 3
0.6897	Remote Similarity	NPD4243	Approved
0.6875	Remote Similarity	NPD3573	Approved
0.6863	Remote Similarity	NPD5696	Approved
0.6837	Remote Similarity	NPD5692	Phase 3
0.6832	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5221	Approved
0.6832	Remote Similarity	NPD5222	Approved
0.6832	Remote Similarity	NPD4697	Phase 3
0.6796	Remote Similarity	NPD5286	Approved
0.6796	Remote Similarity	NPD4696	Approved
0.6796	Remote Similarity	NPD5285	Approved
0.6796	Remote Similarity	NPD4700	Approved
0.6786	Remote Similarity	NPD6317	Approved
0.6768	Remote Similarity	NPD5694	Approved
0.6765	Remote Similarity	NPD5173	Approved
0.6762	Remote Similarity	NPD4754	Approved
0.6742	Remote Similarity	NPD4784	Approved
0.6742	Remote Similarity	NPD6924	Approved
0.6742	Remote Similarity	NPD4785	Approved
0.6742	Remote Similarity	NPD6926	Approved
0.6739	Remote Similarity	NPD4195	Approved
0.6737	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3133	Approved
0.6737	Remote Similarity	NPD3666	Approved
0.6737	Remote Similarity	NPD3665	Phase 1
0.6731	Remote Similarity	NPD5223	Approved
0.6726	Remote Similarity	NPD7327	Approved
0.6726	Remote Similarity	NPD7328	Approved
0.6726	Remote Similarity	NPD6335	Approved
0.6703	Remote Similarity	NPD6116	Phase 1
0.6702	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5290	Discontinued
0.6696	Remote Similarity	NPD6274	Approved
0.6696	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6637	Remote Similarity	NPD7115	Discovery
0.6636	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD4767	Approved
0.6634	Remote Similarity	NPD5707	Approved
0.6632	Remote Similarity	NPD6695	Phase 3
0.6609	Remote Similarity	NPD8377	Approved
0.6609	Remote Similarity	NPD8294	Approved
0.6609	Remote Similarity	NPD6319	Approved
0.6604	Remote Similarity	NPD5174	Approved
0.6604	Remote Similarity	NPD6052	Approved
0.6604	Remote Similarity	NPD5175	Approved
0.66	Remote Similarity	NPD7637	Suspended
0.66	Remote Similarity	NPD5281	Approved
0.66	Remote Similarity	NPD5284	Approved
0.6593	Remote Similarity	NPD6933	Approved
0.6593	Remote Similarity	NPD6117	Approved
0.6579	Remote Similarity	NPD6313	Approved
0.6579	Remote Similarity	NPD6314	Approved
0.6566	Remote Similarity	NPD4753	Phase 2
0.6552	Remote Similarity	NPD8335	Approved
0.6552	Remote Similarity	NPD8380	Approved
0.6552	Remote Similarity	NPD8379	Approved
0.6552	Remote Similarity	NPD8296	Approved
0.6552	Remote Similarity	NPD8378	Approved
0.6552	Remote Similarity	NPD6909	Approved
0.6552	Remote Similarity	NPD8033	Approved
0.6552	Remote Similarity	NPD7503	Approved
0.6552	Remote Similarity	NPD6908	Approved
0.6552	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5141	Approved
0.6538	Remote Similarity	NPD4225	Approved
0.6531	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4221	Approved
0.6526	Remote Similarity	NPD4223	Phase 3
0.6517	Remote Similarity	NPD7152	Approved
0.6517	Remote Similarity	NPD7150	Approved
0.6517	Remote Similarity	NPD7151	Approved
0.6514	Remote Similarity	NPD4730	Approved
0.6514	Remote Similarity	NPD4729	Approved
0.6495	Remote Similarity	NPD1694	Approved
0.6495	Remote Similarity	NPD5329	Approved
0.6491	Remote Similarity	NPD6009	Approved
0.6489	Remote Similarity	NPD7509	Discontinued
0.6489	Remote Similarity	NPD4748	Discontinued
0.6484	Remote Similarity	NPD5275	Approved
0.6484	Remote Similarity	NPD4190	Phase 3
0.6477	Remote Similarity	NPD6923	Approved
0.6477	Remote Similarity	NPD6922	Approved
0.6452	Remote Similarity	NPD6114	Approved
0.6452	Remote Similarity	NPD6118	Approved
0.6452	Remote Similarity	NPD6697	Approved
0.6452	Remote Similarity	NPD6115	Approved
0.6441	Remote Similarity	NPD7604	Phase 2
0.6436	Remote Similarity	NPD6411	Approved
0.6429	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5279	Phase 3
0.6422	Remote Similarity	NPD6412	Phase 2
0.6422	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5983	Phase 2
0.6408	Remote Similarity	NPD5654	Approved
0.6404	Remote Similarity	NPD7143	Approved
0.6404	Remote Similarity	NPD4747	Approved
0.6404	Remote Similarity	NPD7144	Approved
0.6396	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5251	Approved
0.6396	Remote Similarity	NPD5135	Approved
0.6396	Remote Similarity	NPD5248	Approved
0.6396	Remote Similarity	NPD5249	Phase 3
0.6396	Remote Similarity	NPD5247	Approved
0.6396	Remote Similarity	NPD5250	Approved
0.6392	Remote Similarity	NPD4197	Approved
0.6387	Remote Similarity	NPD7492	Approved
0.6383	Remote Similarity	NPD6929	Approved
0.6374	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7750	Discontinued
0.6364	Remote Similarity	NPD5128	Approved
0.6364	Remote Similarity	NPD7524	Approved
0.6333	Remote Similarity	NPD6336	Discontinued
0.6333	Remote Similarity	NPD5777	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