NPASS Compound

Structure

NPC473270 OpenBabel07101719252D 35 39 0 0 1 0 0 0 0 0999 V2000 7.2683 3.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7546 2.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7425 0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1094 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0604 2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8036 1.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9504 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9014 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5956 0.9489 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2072 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3388 0.2798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1583 1.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6446 0.6399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 2 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 25 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 15 24 1 0 0 0 0 16 3 1 1 0 0 0 16 27 1 0 0 0 0 17 13 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 25 1 6 0 0 0 19 26 1 6 0 0 0 20 16 1 1 0 0 0 20 35 1 0 0 0 0 21 26 1 0 0 0 0 21 29 2 0 0 0 0 22 28 1 6 0 0 0 22 30 1 0 0 0 0 23 28 1 1 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 24 35 1 0 0 0 0 25 27 1 1 0 0 0 26 28 1 6 0 0 0 27 33 1 1 0 0 0 28 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.29
Volume:	503.684
LogP:	2.31
LogD:	2.35
LogS:	-3.491
# Rotatable Bonds:	2
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	5.57
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.077
MDCK Permeability:	9.075538400793448e-06
Pgp-inhibitor:	0.961
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.126
30% Bioavailability (F30%):	0.501

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803
Plasma Protein Binding (PPB):	84.09266662597656%
Volume Distribution (VD):	0.998
Pgp-substrate:	7.515647888183594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.849
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.575
CYP3A4-substrate:	0.755

ADMET: Excretion

Clearance (CL):	5.224
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.366
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.711
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.718
Carcinogencity:	0.918
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC473270

Natural Product ID:	NPC473270
*Common Name:**	Tubocapsenolide D
IUPAC Name:	(4S,5S,6S,8S,9S,10R,13S,14S,17S)-4,5,6,17-tetrahydroxy-17-[(1R)-1-[(2R)-6-hydroxy-4,5-dimethyl-3,6-dihydro-2H-pyran-2-yl]ethyl]-10,13-dimethyl-4,6,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-1-one
Synonyms:	tubocapsenolide D
Standard InCHIKey:	KOTKJJXIFZHEFY-BGUSBHMKSA-N
Standard InCHI:	InChI=1S/C28H42O7/c1-14-12-20(35-24(32)15(14)2)16(3)27(33)11-9-18-17-13-23(31)28(34)22(30)7-6-21(29)26(28,5)19(17)8-10-25(18,27)4/h6-7,16-20,22-24,30-34H,8-13H2,1-5H3/t16-,17+,18+,19+,20-,22+,23+,24?,25+,26+,27+,28-/m1/s1
SMILES:	CC1=C(C(OC(C1)C(C)C2(CCC3C2(CCC4C3CC(C5(C4(C(=O)C=CC5O)C)O)O)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389431
PubChem CID:	44423086
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane 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
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	stems, roots, and leaves	Da-Han Mountain, Kaohsiung, Taiwan	2004-OCT	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	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	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[489923]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[489923]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8.01	ug.mL-1	PMID[489923]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	13.49	ug.mL-1	PMID[489923]
NPT27	Others	Unspecified		IC50	=	7.19	ug.mL-1	PMID[489923]

☑ 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 NPC473270 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	233
0.1-0.2	1342
0.2-0.3	3912
0.3-0.4	7643
0.4-0.5	13081
0.5-0.6	7475
0.6-0.7	6144
0.7-0.8	2663
0.8-0.85	166
0.85-0.9	31
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC473256
0.9643	High Similarity	NPC470878
0.9464	High Similarity	NPC473274
0.9279	High Similarity	NPC147912
0.9279	High Similarity	NPC67259
0.9123	High Similarity	NPC264954
0.9043	High Similarity	NPC474370
0.8947	High Similarity	NPC286528
0.8947	High Similarity	NPC140055
0.8947	High Similarity	NPC167606
0.8947	High Similarity	NPC470492
0.8947	High Similarity	NPC20302
0.8898	High Similarity	NPC3381
0.8889	High Similarity	NPC88326
0.8889	High Similarity	NPC153700
0.887	High Similarity	NPC50774
0.887	High Similarity	NPC709
0.886	High Similarity	NPC64318
0.885	High Similarity	NPC122056
0.8783	High Similarity	NPC470493
0.8783	High Similarity	NPC312824
0.8783	High Similarity	NPC183580
0.8761	High Similarity	NPC191620
0.876	High Similarity	NPC473593
0.876	High Similarity	NPC476966
0.8739	High Similarity	NPC8374
0.8673	High Similarity	NPC474315
0.8644	High Similarity	NPC67569
0.8621	High Similarity	NPC470959
0.8621	High Similarity	NPC476965
0.8618	High Similarity	NPC231240
0.8607	High Similarity	NPC471407
0.8583	High Similarity	NPC172154
0.8583	High Similarity	NPC81736
0.8571	High Similarity	NPC269642
0.8571	High Similarity	NPC23786
0.8571	High Similarity	NPC470265
0.8548	High Similarity	NPC316915
0.8547	High Similarity	NPC257457
0.8547	High Similarity	NPC186525
0.8547	High Similarity	NPC329736
0.8547	High Similarity	NPC311554
0.8512	High Similarity	NPC293112
0.8509	High Similarity	NPC470961
0.85	High Similarity	NPC204812
0.85	High Similarity	NPC11895
0.85	High Similarity	NPC469789
0.8496	Intermediate Similarity	NPC214644
0.8487	Intermediate Similarity	NPC46570
0.8482	Intermediate Similarity	NPC91034
0.8475	Intermediate Similarity	NPC475041
0.8475	Intermediate Similarity	NPC61520
0.8468	Intermediate Similarity	NPC471855
0.8462	Intermediate Similarity	NPC471854
0.8462	Intermediate Similarity	NPC243065
0.843	Intermediate Similarity	NPC8369
0.843	Intermediate Similarity	NPC241456
0.843	Intermediate Similarity	NPC32868
0.843	Intermediate Similarity	NPC470494
0.8421	Intermediate Similarity	NPC29133
0.8417	Intermediate Similarity	NPC28532
0.8417	Intermediate Similarity	NPC170538
0.8417	Intermediate Similarity	NPC107493
0.8403	Intermediate Similarity	NPC476961
0.8387	Intermediate Similarity	NPC173347
0.8376	Intermediate Similarity	NPC270929
0.8374	Intermediate Similarity	NPC311534
0.8306	Intermediate Similarity	NPC231529
0.8305	Intermediate Similarity	NPC218970
0.8293	Intermediate Similarity	NPC287423
0.8293	Intermediate Similarity	NPC156797
0.8291	Intermediate Similarity	NPC284915
0.8288	Intermediate Similarity	NPC477915
0.8276	Intermediate Similarity	NPC69291
0.8261	Intermediate Similarity	NPC37116
0.8246	Intermediate Similarity	NPC177064
0.8246	Intermediate Similarity	NPC472825
0.8235	Intermediate Similarity	NPC475913
0.823	Intermediate Similarity	NPC60681
0.823	Intermediate Similarity	NPC149047
0.8226	Intermediate Similarity	NPC473620
0.8226	Intermediate Similarity	NPC245094
0.8214	Intermediate Similarity	NPC26478
0.8211	Intermediate Similarity	NPC473635
0.8197	Intermediate Similarity	NPC473979
0.8182	Intermediate Similarity	NPC470418
0.8174	Intermediate Similarity	NPC475065
0.8167	Intermediate Similarity	NPC474179
0.8167	Intermediate Similarity	NPC475834
0.8158	Intermediate Similarity	NPC330011
0.8158	Intermediate Similarity	NPC475060
0.8158	Intermediate Similarity	NPC83744
0.8158	Intermediate Similarity	NPC477916
0.8158	Intermediate Similarity	NPC473284
0.8158	Intermediate Similarity	NPC220229
0.8158	Intermediate Similarity	NPC144459
0.8158	Intermediate Similarity	NPC329048
0.8151	Intermediate Similarity	NPC55296
0.8151	Intermediate Similarity	NPC239273
0.8145	Intermediate Similarity	NPC470882
0.8145	Intermediate Similarity	NPC305496
0.8142	Intermediate Similarity	NPC209502
0.8142	Intermediate Similarity	NPC204833
0.8136	Intermediate Similarity	NPC475163
0.813	Intermediate Similarity	NPC318135
0.8125	Intermediate Similarity	NPC185530
0.8125	Intermediate Similarity	NPC473424
0.812	Intermediate Similarity	NPC475524
0.812	Intermediate Similarity	NPC476163
0.812	Intermediate Similarity	NPC236217
0.812	Intermediate Similarity	NPC207251
0.812	Intermediate Similarity	NPC100267
0.8103	Intermediate Similarity	NPC76084
0.8099	Intermediate Similarity	NPC79579
0.8099	Intermediate Similarity	NPC281840
0.8099	Intermediate Similarity	NPC476962
0.8087	Intermediate Similarity	NPC318363
0.8087	Intermediate Similarity	NPC473482
0.8087	Intermediate Similarity	NPC329417
0.8087	Intermediate Similarity	NPC217201
0.8087	Intermediate Similarity	NPC475418
0.8087	Intermediate Similarity	NPC220155
0.8083	Intermediate Similarity	NPC45475
0.8083	Intermediate Similarity	NPC153440
0.807	Intermediate Similarity	NPC214264
0.807	Intermediate Similarity	NPC85829
0.807	Intermediate Similarity	NPC257353
0.807	Intermediate Similarity	NPC150531
0.807	Intermediate Similarity	NPC166607
0.807	Intermediate Similarity	NPC302607
0.807	Intermediate Similarity	NPC49958
0.807	Intermediate Similarity	NPC48733
0.807	Intermediate Similarity	NPC296945
0.807	Intermediate Similarity	NPC97202
0.807	Intermediate Similarity	NPC171137
0.807	Intermediate Similarity	NPC202167
0.807	Intermediate Similarity	NPC50692
0.807	Intermediate Similarity	NPC260268
0.807	Intermediate Similarity	NPC476027
0.807	Intermediate Similarity	NPC152695
0.807	Intermediate Similarity	NPC319077
0.8067	Intermediate Similarity	NPC148458
0.8067	Intermediate Similarity	NPC190286
0.8053	Intermediate Similarity	NPC475050
0.8053	Intermediate Similarity	NPC311612
0.8051	Intermediate Similarity	NPC260665
0.8051	Intermediate Similarity	NPC317210
0.8051	Intermediate Similarity	NPC250109
0.8051	Intermediate Similarity	NPC962
0.8034	Intermediate Similarity	NPC471243
0.8033	Intermediate Similarity	NPC129434
0.8017	Intermediate Similarity	NPC11710
0.8017	Intermediate Similarity	NPC5292
0.8017	Intermediate Similarity	NPC476960
0.8017	Intermediate Similarity	NPC230513
0.8016	Intermediate Similarity	NPC104382
0.8	Intermediate Similarity	NPC117702
0.8	Intermediate Similarity	NPC473265
0.8	Intermediate Similarity	NPC301666
0.8	Intermediate Similarity	NPC471357
0.8	Intermediate Similarity	NPC146456
0.8	Intermediate Similarity	NPC473253
0.8	Intermediate Similarity	NPC185
0.8	Intermediate Similarity	NPC42399
0.8	Intermediate Similarity	NPC469757
0.7984	Intermediate Similarity	NPC470922
0.7983	Intermediate Similarity	NPC243354
0.7983	Intermediate Similarity	NPC477580
0.7983	Intermediate Similarity	NPC326542
0.7982	Intermediate Similarity	NPC75531
0.7982	Intermediate Similarity	NPC294259
0.7982	Intermediate Similarity	NPC160843
0.7982	Intermediate Similarity	NPC149124
0.7967	Intermediate Similarity	NPC470419
0.7966	Intermediate Similarity	NPC205534
0.7965	Intermediate Similarity	NPC87351
0.7953	Intermediate Similarity	NPC196921
0.7953	Intermediate Similarity	NPC220757
0.7951	Intermediate Similarity	NPC268530
0.7951	Intermediate Similarity	NPC154491
0.7951	Intermediate Similarity	NPC471406
0.7951	Intermediate Similarity	NPC474585
0.7949	Intermediate Similarity	NPC473627
0.7949	Intermediate Similarity	NPC16270
0.7949	Intermediate Similarity	NPC235014
0.7946	Intermediate Similarity	NPC154072
0.7946	Intermediate Similarity	NPC476299
0.7946	Intermediate Similarity	NPC474012
0.7939	Intermediate Similarity	NPC75616
0.7937	Intermediate Similarity	NPC473888
0.7934	Intermediate Similarity	NPC473617
0.7934	Intermediate Similarity	NPC475632
0.7934	Intermediate Similarity	NPC473828
0.7934	Intermediate Similarity	NPC146786
0.7934	Intermediate Similarity	NPC113448
0.7934	Intermediate Similarity	NPC86020
0.7931	Intermediate Similarity	NPC300614
0.7931	Intermediate Similarity	NPC65941
0.7931	Intermediate Similarity	NPC90946
0.7928	Intermediate Similarity	NPC253826

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 NPC473270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1496
0.2-0.3	3629
0.3-0.4	2552
0.4-0.5	746
0.5-0.6	244
0.6-0.7	147
0.7-0.8	133
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD7115	Discovery
0.7967	Intermediate Similarity	NPD6370	Approved
0.7874	Intermediate Similarity	NPD7319	Approved
0.7845	Intermediate Similarity	NPD6412	Phase 2
0.7815	Intermediate Similarity	NPD6882	Approved
0.7807	Intermediate Similarity	NPD5211	Phase 2
0.7805	Intermediate Similarity	NPD6054	Approved
0.7795	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD6899	Approved
0.7778	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD7507	Approved
0.7742	Intermediate Similarity	NPD7503	Approved
0.7731	Intermediate Similarity	NPD6649	Approved
0.7731	Intermediate Similarity	NPD6650	Approved
0.7699	Intermediate Similarity	NPD4225	Approved
0.7692	Intermediate Similarity	NPD5697	Approved
0.7672	Intermediate Similarity	NPD5141	Approved
0.7667	Intermediate Similarity	NPD8297	Approved
0.7647	Intermediate Similarity	NPD7102	Approved
0.7647	Intermediate Similarity	NPD7290	Approved
0.7647	Intermediate Similarity	NPD6883	Approved
0.7647	Intermediate Similarity	NPD4634	Approved
0.7632	Intermediate Similarity	NPD5286	Approved
0.7632	Intermediate Similarity	NPD4696	Approved
0.7632	Intermediate Similarity	NPD5285	Approved
0.7607	Intermediate Similarity	NPD6675	Approved
0.7607	Intermediate Similarity	NPD6402	Approved
0.7607	Intermediate Similarity	NPD7128	Approved
0.7607	Intermediate Similarity	NPD5739	Approved
0.76	Intermediate Similarity	NPD6016	Approved
0.76	Intermediate Similarity	NPD6015	Approved
0.7583	Intermediate Similarity	NPD6617	Approved
0.7583	Intermediate Similarity	NPD6847	Approved
0.7583	Intermediate Similarity	NPD8130	Phase 1
0.7583	Intermediate Similarity	NPD6869	Approved
0.7581	Intermediate Similarity	NPD7516	Approved
0.7563	Intermediate Similarity	NPD6372	Approved
0.7563	Intermediate Similarity	NPD6373	Approved
0.7563	Intermediate Similarity	NPD6013	Approved
0.7563	Intermediate Similarity	NPD6012	Approved
0.7563	Intermediate Similarity	NPD6014	Approved
0.7559	Intermediate Similarity	NPD7492	Approved
0.754	Intermediate Similarity	NPD5988	Approved
0.752	Intermediate Similarity	NPD6059	Approved
0.752	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.7479	Intermediate Similarity	NPD6011	Approved
0.7479	Intermediate Similarity	NPD7320	Approved
0.7478	Intermediate Similarity	NPD7640	Approved
0.7478	Intermediate Similarity	NPD7639	Approved
0.7477	Intermediate Similarity	NPD6079	Approved
0.746	Intermediate Similarity	NPD8033	Approved
0.7456	Intermediate Similarity	NPD6083	Phase 2
0.7456	Intermediate Similarity	NPD4755	Approved
0.7456	Intermediate Similarity	NPD6084	Phase 2
0.7442	Intermediate Similarity	NPD7078	Approved
0.7442	Intermediate Similarity	NPD8293	Discontinued
0.7436	Intermediate Similarity	NPD5175	Approved
0.7436	Intermediate Similarity	NPD5174	Approved
0.7434	Intermediate Similarity	NPD4629	Approved
0.7434	Intermediate Similarity	NPD5210	Approved
0.7414	Intermediate Similarity	NPD5223	Approved
0.7411	Intermediate Similarity	NPD4202	Approved
0.7395	Intermediate Similarity	NPD5701	Approved
0.7391	Intermediate Similarity	NPD7638	Approved
0.7387	Intermediate Similarity	NPD5785	Approved
0.7381	Intermediate Similarity	NPD8294	Approved
0.7381	Intermediate Similarity	NPD8377	Approved
0.7339	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD3618	Phase 1
0.7333	Intermediate Similarity	NPD6686	Approved
0.7328	Intermediate Similarity	NPD4700	Approved
0.7323	Intermediate Similarity	NPD8379	Approved
0.7323	Intermediate Similarity	NPD8296	Approved
0.7323	Intermediate Similarity	NPD8380	Approved
0.7323	Intermediate Similarity	NPD8378	Approved
0.7323	Intermediate Similarity	NPD8335	Approved
0.7317	Intermediate Similarity	NPD4632	Approved
0.7297	Intermediate Similarity	NPD4753	Phase 2
0.7297	Intermediate Similarity	NPD5328	Approved
0.728	Intermediate Similarity	NPD6009	Approved
0.7257	Intermediate Similarity	NPD6399	Phase 3
0.7241	Intermediate Similarity	NPD5696	Approved
0.7217	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5221	Approved
0.7217	Intermediate Similarity	NPD5222	Approved
0.719	Intermediate Similarity	NPD4730	Approved
0.719	Intermediate Similarity	NPD4729	Approved
0.7188	Intermediate Similarity	NPD8513	Phase 3
0.7165	Intermediate Similarity	NPD7100	Approved
0.7165	Intermediate Similarity	NPD7101	Approved
0.7156	Intermediate Similarity	NPD3666	Approved
0.7156	Intermediate Similarity	NPD3133	Approved
0.7156	Intermediate Similarity	NPD4786	Approved
0.7156	Intermediate Similarity	NPD3665	Phase 1
0.7155	Intermediate Similarity	NPD5173	Approved
0.7154	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5695	Phase 3
0.7087	Intermediate Similarity	NPD6335	Approved
0.7077	Intermediate Similarity	NPD8328	Phase 3
0.7073	Intermediate Similarity	NPD5251	Approved
0.7073	Intermediate Similarity	NPD5250	Approved
0.7073	Intermediate Similarity	NPD5248	Approved
0.7073	Intermediate Similarity	NPD5249	Phase 3
0.7073	Intermediate Similarity	NPD6371	Approved
0.7073	Intermediate Similarity	NPD5247	Approved
0.7069	Intermediate Similarity	NPD4697	Phase 3
0.7063	Intermediate Similarity	NPD6274	Approved
0.7054	Intermediate Similarity	NPD8516	Approved
0.7054	Intermediate Similarity	NPD8517	Approved
0.7054	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD8515	Approved
0.7049	Intermediate Similarity	NPD5128	Approved
0.7043	Intermediate Similarity	NPD7748	Approved
0.704	Intermediate Similarity	NPD8133	Approved
0.7027	Intermediate Similarity	NPD7521	Approved
0.7027	Intermediate Similarity	NPD7334	Approved
0.7027	Intermediate Similarity	NPD6684	Approved
0.7027	Intermediate Similarity	NPD6409	Approved
0.7027	Intermediate Similarity	NPD7146	Approved
0.7027	Intermediate Similarity	NPD5330	Approved
0.7025	Intermediate Similarity	NPD4768	Approved
0.7025	Intermediate Similarity	NPD4767	Approved
0.7025	Intermediate Similarity	NPD6008	Approved
0.7018	Intermediate Similarity	NPD5693	Phase 1
0.7018	Intermediate Similarity	NPD7515	Phase 2
0.7016	Intermediate Similarity	NPD5217	Approved
0.7016	Intermediate Similarity	NPD5216	Approved
0.7016	Intermediate Similarity	NPD5215	Approved
0.7009	Intermediate Similarity	NPD7902	Approved
0.7008	Intermediate Similarity	NPD6317	Approved
0.7	Intermediate Similarity	NPD4754	Approved
0.6992	Remote Similarity	NPD6033	Approved
0.6992	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4223	Phase 3
0.6972	Remote Similarity	NPD4221	Approved
0.6972	Remote Similarity	NPD3667	Approved
0.696	Remote Similarity	NPD6053	Discontinued
0.6953	Remote Similarity	NPD6313	Approved
0.6953	Remote Similarity	NPD6314	Approved
0.6947	Remote Similarity	NPD7604	Phase 2
0.6947	Remote Similarity	NPD6067	Discontinued
0.6937	Remote Similarity	NPD5329	Approved
0.6937	Remote Similarity	NPD5363	Approved
0.6935	Remote Similarity	NPD5169	Approved
0.6935	Remote Similarity	NPD5135	Approved
0.6935	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5983	Phase 2
0.6917	Remote Similarity	NPD7632	Discontinued
0.6911	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6903	Approved
0.688	Remote Similarity	NPD5127	Approved
0.6875	Remote Similarity	NPD5690	Phase 2
0.687	Remote Similarity	NPD5284	Approved
0.687	Remote Similarity	NPD5281	Approved
0.6847	Remote Similarity	NPD4197	Approved
0.6842	Remote Similarity	NPD6673	Approved
0.6842	Remote Similarity	NPD6080	Approved
0.6842	Remote Similarity	NPD6336	Discontinued
0.6842	Remote Similarity	NPD6904	Approved
0.68	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6868	Approved
0.6794	Remote Similarity	NPD6909	Approved
0.6794	Remote Similarity	NPD6908	Approved
0.6786	Remote Similarity	NPD1694	Approved
0.6769	Remote Similarity	NPD4522	Approved
0.6765	Remote Similarity	NPD5956	Approved
0.6757	Remote Similarity	NPD4788	Approved
0.6754	Remote Similarity	NPD6672	Approved
0.6754	Remote Similarity	NPD5737	Approved
0.6752	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6001	Approved
0.6752	Remote Similarity	NPD7900	Approved
0.6744	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4138	Approved
0.6726	Remote Similarity	NPD4689	Approved
0.6726	Remote Similarity	NPD5205	Approved
0.6726	Remote Similarity	NPD4693	Phase 3
0.6726	Remote Similarity	NPD4688	Approved
0.6726	Remote Similarity	NPD4690	Approved
0.6724	Remote Similarity	NPD8034	Phase 2
0.6724	Remote Similarity	NPD7637	Suspended
0.6724	Remote Similarity	NPD8035	Phase 2
0.6719	Remote Similarity	NPD5167	Approved
0.6697	Remote Similarity	NPD4195	Approved
0.6696	Remote Similarity	NPD6051	Approved
0.6696	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.664	Remote Similarity	NPD5168	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